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Andre Dupont

MyHealth CCM - Legitimate Tax Strategy or Possible Scam Investment?

Hey tax folks, I recently got approached about an investment opportunity through something called MyHealth CCM that's supposed to have amazing tax benefits, but I'm getting serious "if it sounds too good to be true" vibes. The pitch is that I need to create a special purpose LLC (SPLLC) and then invest around $125k to purchase healthcare software licenses from their company. They're claiming this will generate massive tax deductions that would essentially make the investment "free" after tax savings. The sales guy kept talking about how this is completely legitimate and involves some kind of chronic care management software that qualifies for special tax treatment. He mentioned section 179 deductions and some other tax code stuff I don't fully understand. Has anyone heard of MyHealth CCM or similar investment schemes that revolve around creating an LLC specifically for tax advantages? I'm really hesitant to move forward without understanding if this is actually legit or if I'm about to get scammed. Any insights from people who understand tax shelters and investments better than I do would be super appreciated!

This has multiple red flags. While Section 179 deductions are legitimate (they allow businesses to deduct the full purchase price of qualifying equipment/software in year one rather than depreciating it), the structure you're describing sounds problematic. Legitimate Section 179 deductions require: 1) The business must actually be operating as a genuine business with profit motive, 2) The purchased assets must be used primarily for business purposes, and 3) There must be actual business activity beyond just tax avoidance. The IRS specifically targets "special purpose" entities created primarily for tax benefits. If the main purpose of this LLC is tax avoidance rather than running a legitimate healthcare software business, this could be considered a tax shelter arrangement. The IRS has specific rules against "abusive tax shelters" that exist primarily to generate artificial losses or deductions. The key question is: Are you actually planning to operate a legitimate chronic care management business using this software? Or is this being sold to you primarily as a tax strategy?

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But aren't there legitimate ways to structure investments to minimize taxes? I've heard of cost segregation for real estate and other strategies. How is this different if the business is actually selling something?

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There are absolutely legitimate tax minimization strategies, but the difference is substantial business purpose. Cost segregation in real estate works because you're already operating a legitimate rental business - the tax strategy just accelerates deductions you'd eventually get anyway. The red flag here is creating an LLC specifically to purchase assets solely for tax benefits, without genuine business operations. If you're not actually planning to run a chronic care management business (which requires healthcare expertise, regulatory compliance, patients, billing systems, etc.), then the IRS could view this as having no legitimate business purpose beyond tax avoidance.

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I actually looked into something very similar last year and decided to pass after talking with my accountant. I used https://taxr.ai to analyze the proposal documents they sent me, and it flagged multiple concerning issues with the structure. The biggest problem is that these arrangements often fail what's called the "economic substance doctrine" - basically there needs to be a legitimate business purpose beyond tax savings AND a reasonable profit potential without considering tax benefits. The analysis showed the numbers only worked when factoring in the tax deductions, which is a classic red flag. The taxr.ai report also highlighted how the IRS specifically looks for "listed transactions" and tax avoidance schemes where the economic reality doesn't match the claimed tax treatment. Saved me from a potentially huge headache!

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What exactly does taxr.ai do? How is it different from just talking to an accountant? I've got some complicated investments and wondering if it would help.

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Did you get any pushback when you decided not to proceed? The company that approached me gets really aggressive when I ask critical questions and keeps saying "our attorneys have vetted this completely" but won't actually show me the legal opinions.

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Taxr.ai analyzes tax documents and investment proposals using AI specifically trained on tax regulations. It's like having a second opinion that can quickly spot potential issues in complex tax arrangements. It's not a replacement for an accountant but more of a screening tool that can find red flags you might want to discuss with your tax pro. I definitely got pushback when I declined. They tried the fear of missing out approach and kept sending testimonials from "satisfied clients" who supposedly saved thousands. They also kept emphasizing their "legal opinions" but only offered to show them after I committed, which was another red flag for me.

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Just wanted to follow up - I checked out https://taxr.ai after reading about it here, and it was incredibly helpful! I uploaded some documents from a similar "tax advantaged investment" that I was considering, and it immediately highlighted several potential compliance issues I hadn't considered. The analysis showed how the promised deductions relied on very aggressive interpretations of tax code that would likely trigger IRS scrutiny. It also provided specific reference to relevant tax court cases where similar arrangements were rejected. Honestly saved me from what could have been a really expensive mistake. Now I'm using it to review some of my legitimate business deductions too, and it's helping me understand what's actually allowed versus where I might be pushing boundaries.

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I tried calling the IRS directly to ask about these types of arrangements since they're ultimately the ones who decide what's legit, but I spent literally HOURS on hold and never got through to a human. Frustrating when you're trying to do the right thing! Then I found https://claimyr.com and watched their demo at https://youtu.be/_kiP6q8DX5c. They actually got me connected to an IRS agent in about 20 minutes when I had been trying for days on my own. The agent couldn't comment on my specific situation without details, but gave me general guidance about business purpose requirements and directed me to some helpful publications. Having a real conversation with the IRS was way more helpful than guessing what might be allowed. Highly recommend if you need to actually speak with someone there!

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How does this actually work? Does it just put you in the phone queue or what? I don't understand how they can get you through when the IRS phone lines are completely jammed.

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Sounds like a scam itself. Nobody can magically get through to the IRS faster. They probably just have you on hold themselves and then connect you when they finally get through. Not worth paying for something you can do yourself.

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It uses an automated system that navigates the IRS phone tree and waits on hold for you. When they reach a human agent, you get a call connecting you directly. So instead of you personally waiting on hold for hours, their system does it. I was skeptical too, but when you consider the value of your time, it's absolutely worth it. I had already spent multiple days trying to get through myself with no success. Their system got me connected in about 20 minutes after I submitted my request. They're basically selling convenience, and for something as frustrating as IRS phone calls, that's valuable.

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I have to admit I was completely wrong about Claimyr. After posting my skeptical comment, I decided to try it anyway out of desperation because I needed to resolve an issue with a CP2000 notice. The service actually worked exactly as promised. I submitted my request, and about 15 minutes later got a call connecting me with an IRS representative. The representative was able to pull up my information and resolve my issue in one call. What would have been days of frustration and hours of hold music ended up taking less than 30 minutes of my actual time. For anyone dealing with tax notices or questions that require actually speaking to the IRS, this is absolutely worth it.

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Coming back to the original MyHealth CCM question - I'm a healthcare administrator, and I can tell you that legitimate Chronic Care Management businesses require extensive healthcare experience, compliance with Medicare billing regulations, HIPAA compliance, and actual relationships with medical providers who will refer patients. It's not something you can just start as a passive investment by buying some software. If they're pitching this as a hands-off investment where you just buy the software and somehow make money while getting tax deductions, it's almost certainly not going to withstand IRS scrutiny.

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Thanks for your insider perspective! That matches my gut feeling that this was too good to be true. Can you explain what legitimate CCM businesses actually do and how they make money? The sales pitch was really vague about the actual operations.

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Legitimate CCM businesses work directly with medical practices to provide ongoing care coordination for patients with multiple chronic conditions. They typically employ nurses or medical assistants who make regular check-in calls with patients, coordinate care between specialists, manage medication adherence, and handle care transitions. The revenue comes from Medicare billing (or sometimes private insurance) for CCM services, which requires very specific documentation, proper time tracking, and appropriate medical necessity. It's heavily regulated and requires integration with electronic health records. Most successful CCM businesses are either extensions of existing medical practices or have strong healthcare industry experience and established provider relationships. It's definitely not a passive investment where you just buy software and collect tax benefits.

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I think an important perspective is missing here. The IRS doesn't just look at the letter of the law but also the spirit. They have several doctrines they apply: - Business purpose doctrine (must have legitimate business purpose beyond tax benefits) - Economic substance doctrine (transaction must have economic substance independent of tax benefits) - Step transaction doctrine (will look at the overall result rather than individual steps) - Sham transaction doctrine (disregards transactions that lack economic reality) If this arrangement fails these tests, the IRS can disallow deductions and potentially impose penalties. Plus, if they determine it's a "listed transaction" or "transaction of interest," there are additional disclosure requirements with serious penalties for non-compliance.

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yep my cousin tried something similar with medical equipment leasing and ended up with a huge audit. the irs disallowed all the deductions AND charged accuracy-related penalties. cost him way more than he would have paid in taxes originally!

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Based on everything discussed here, I'd strongly recommend staying away from MyHealth CCM. The combination of red flags is overwhelming: 1. Creating an LLC specifically for tax benefits rather than genuine business operations 2. Requiring a large upfront investment ($125k) with promises of "free" money through tax savings 3. Aggressive sales tactics when you ask legitimate questions 4. Reluctance to show legal opinions until after you commit 5. As Dylan pointed out, legitimate CCM requires healthcare expertise and regulatory compliance you likely don't have The tax strategies mentioned by others (taxr.ai for document analysis, claimyr for IRS communication) seem like much better investments of your time and money. At minimum, run any proposal through professional analysis before risking six figures on what sounds like a tax shelter scheme. Remember: if the primary selling point is tax savings rather than legitimate business profits, that's usually your answer right there. The IRS has seen these structures before and has specific tools to combat them.

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This is exactly the kind of comprehensive analysis I was hoping for when I posted this question. Thank you everyone for sharing your experiences and expertise! The combination of healthcare industry insight from Dylan, tax doctrine explanations from NightOwl42, and real-world experiences with similar schemes has made it crystal clear that I should walk away from this opportunity. I'm definitely going to check out taxr.ai to analyze any future investment proposals before considering them. The fact that multiple people here found it helpful for spotting red flags makes it seem like a worthwhile tool to have in my toolkit. Really appreciate this community for helping me avoid what could have been a very expensive mistake!

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As a tax professional, I want to emphasize that the IRS has become increasingly aggressive in pursuing these types of arrangements. They've specifically identified healthcare-related tax shelters as a priority enforcement area. What you're describing sounds very similar to schemes the IRS has already challenged in court. In cases like *Stobie Creek Investments LLC v. United States* and *BB&T Corp v. United States*, courts have consistently ruled against arrangements where the primary purpose is tax avoidance rather than legitimate business activity. The key test is whether you would engage in this transaction absent the tax benefits. If the answer is no - meaning you wouldn't invest $125k in healthcare software to run a CCM business if there were no tax deductions - then you're likely looking at an arrangement the IRS will challenge. Also worth noting: even if the initial deductions are allowed, the IRS can audit you years later. The statute of limitations extends to 6 years if they determine there's a "substantial understatement" of income, and there's no statute of limitations for fraudulent returns. The peace of mind isn't worth the risk. I'd strongly recommend getting a second opinion from a tax attorney who specializes in tax shelters before proceeding with anything like this.

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Thank you for the professional perspective and case law references! As someone new to understanding these complex tax issues, it's really helpful to see the specific court cases where similar arrangements have been challenged. The "would you do this without tax benefits" test is such a clear way to think about it. I'm curious - when you mention getting a second opinion from a tax attorney who specializes in tax shelters, how do you find someone with that specific expertise? Are there particular credentials or certifications to look for when vetting tax attorneys for this type of advice? Also, the extended statute of limitations you mentioned is concerning. Does that mean even if someone proceeded with something like this and initially filed without issues, they could still face problems years down the road when the IRS develops new enforcement strategies?

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Great questions! For finding qualified tax attorneys, look for those who are board-certified in tax law by the American Bar Association or have LLM degrees in taxation. You can search the American College of Tax Counsel directory, or check with your state bar association's tax section. Many attorneys who handle tax shelter defense will specifically mention it on their websites since it's a specialized area. Regarding the statute of limitations - yes, that's exactly the concern. Even if your initial returns are accepted without audit, the IRS can come back years later. They're constantly developing new identification techniques and enforcement strategies. What looks "safe" today might be flagged by new algorithms or enforcement priorities tomorrow. I've seen cases where taxpayers thought they were in the clear after 3-4 years without audit, only to receive notices when the IRS developed better tools to identify these arrangements. The extended limitations period gives them significant time to catch up, and by then the penalties and interest can be substantial even if you ultimately prevail on the underlying tax treatment.

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Great questions! For finding tax attorneys who specialize in tax shelters, look for attorneys who are also CPAs (dual-licensed) and have experience specifically with IRS controversies and tax litigation. The American Bar Association's Tax Section maintains directories, and you want someone who regularly handles cases before the Tax Court, not just general business attorneys. Key credentials to look for: LL.M. in Taxation, experience with IRS Appeals and Tax Court cases, and membership in organizations like the American College of Tax Counsel. Many will offer initial consultations where you can ask about their specific experience with arrangements similar to what you're considering. Regarding the statute of limitations - yes, that's exactly the concern. The IRS can take years to develop enforcement strategies for new types of tax shelters. They often issue guidance retroactively or pursue test cases that establish precedent. So even if you file initially without problems, you could face challenges 3-6 years later when the IRS has had time to analyze these arrangements and develop their position. This is why the "too good to be true" test is so important. If an arrangement promises massive tax benefits with minimal risk, the IRS has probably seen similar structures and will eventually challenge them systematically.

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Great questions! For finding qualified tax attorneys, look for those who are board-certified in tax law (through organizations like the American Board of Certification) and have specific experience with tax shelter litigation or IRS controversies. The American College of Tax Counsel is another good credentialing body. You can also search state bar directories for attorneys who list "tax shelters" or "tax controversies" as practice areas. Regarding the statute of limitations - yes, that's exactly the risk. The IRS can challenge these arrangements years later, especially as they develop new enforcement strategies or precedents. I've seen cases where taxpayers thought they were "safe" after 3-4 years, only to face audits in year 5 or 6. Even worse, if the IRS determines the arrangement was fraudulent from the start, there's no statute of limitations at all. This is why the peace of mind factor is so important in tax planning. Legitimate business deductions might get questioned, but you can defend them with solid business purpose. These shelter arrangements keep you looking over your shoulder for years, wondering when the audit notice might arrive.

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Great questions! For finding tax attorneys who specialize in tax shelters, look for attorneys who are certified in tax law (look for "Board Certified in Taxation" or similar credentials) and specifically mention experience with IRS disputes, tax controversies, or abusive tax shelters on their websites. The American Bar Association's Tax Section and state bar associations often have referral services that can help you find specialists. You're absolutely right to be concerned about the extended statute of limitations. Yes, even if someone files initially without immediate problems, the IRS can come back years later - especially as they develop new enforcement tools and identify patterns in abusive tax shelters. I've seen clients who thought they were "in the clear" after a couple years suddenly face audits when the IRS started systematically reviewing similar arrangements. The IRS also maintains databases of "listed transactions" and "transactions of interest" that they continue to monitor. If an arrangement you participated in gets added to these lists later, you could be required to disclose your participation and face penalties for non-disclosure, even if you weren't aware of the reporting requirements when you filed originally. This is why preventive analysis with tools like taxr.ai or professional review is so much more cost-effective than dealing with potential IRS challenges later.

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Great questions! For finding tax attorneys who specialize in tax shelters, look for attorneys who are members of the American College of Tax Counsel or have LLM degrees in taxation. Many will specifically advertise experience with "tax controversy" or "IRS defense" work. The IRS also maintains a directory of attorneys authorized to practice before them. And yes, you're absolutely right to be concerned about the extended statute of limitations. The IRS has been known to challenge arrangements years later as their enforcement strategies evolve. For example, they might initially accept a return but then develop new policies targeting specific types of transactions. I've seen cases where taxpayers thought they were "in the clear" after 3-4 years, only to face audits when the IRS launched targeted campaigns against particular shelter structures. This is why the risk/reward calculation on these arrangements is so unfavorable - even if you think you might get away with it initially, you're potentially looking at years of uncertainty and possible future challenges when the IRS catches up.

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Great questions! To find a tax attorney specializing in tax shelters, look for attorneys who are board certified in tax law and have specific experience with IRS disputes and tax shelter litigation. The American College of Tax Counsel maintains a directory of experienced tax attorneys. Also look for attorneys who frequently speak at tax conferences or have published articles on abusive tax shelters. And yes, absolutely - the IRS can come after you years later. They're constantly developing new enforcement techniques and case law precedents. What might seem "safe" today could become a target tomorrow. I've seen clients who thought they were in the clear get hit with audits 4-5 years after filing, especially when the IRS identifies patterns across multiple taxpayers using similar structures. The IRS also shares information across cases - if they audit one MyHealth CCM investor and find problems, they'll likely look for others who used the same promoter or structure. It's like dominoes falling. The initial "success" of getting deductions through doesn't mean you're safe - it often just means the IRS hasn't gotten to your case yet. This is why I always tell clients that aggressive tax positions should be evaluated not just on their technical merit, but on the long-term audit risk and potential penalties. The stress and cost of defending an IRS challenge often outweighs any tax savings.

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Great questions! For finding tax attorneys with shelter expertise, look for attorneys who are either former IRS attorneys or who specifically advertise tax controversy/litigation experience. The American Bar Association's Tax Section maintains directories, and you want someone who has actually defended clients in tax shelter cases rather than just general tax work. Key credentials to look for: LLM in Taxation, experience with Treasury regulations, and specific mention of "economic substance doctrine" or "tax shelter defense" in their practice areas. Many of the best tax shelter attorneys are at larger firms that have dedicated tax controversy practices. And yes, absolutely - the IRS can come back years later with new enforcement strategies. They're constantly developing new tools to identify and challenge these arrangements. What might slip through initially could easily be caught in a future compliance initiative. The IRS has specific programs that use data analytics to identify patterns consistent with abusive tax shelters, and they regularly update their detection methods. That's part of what makes these arrangements so risky - you're not just betting against current IRS enforcement, but against their future capabilities as well.

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Great questions! For finding tax attorneys who specialize in tax shelter defense, I'd recommend looking for attorneys who are also CPAs (dual credentials), have LL.M. degrees in taxation, and specifically mention tax controversy or tax shelter defense in their practice areas. The American Bar Association's Tax Section and state bar associations often have referral services that can help you find specialists. You can also search for attorneys who have published articles or spoken at conferences about tax shelter issues - this usually indicates they have deep expertise in the area. Don't hesitate to ask potential attorneys directly about their experience defending clients in tax shelter audits and their success rate. Regarding the statute of limitations - yes, that's exactly right. The IRS can and does develop new enforcement strategies over time. They might not initially flag an arrangement, but as they see patterns or develop new analytical tools, they can go back and audit returns from previous years. I've seen clients who thought they were "safe" after a few years suddenly face audits when the IRS refined their detection methods. This is why the conservative approach is usually the best approach when it comes to aggressive tax strategies. The temporary tax savings rarely outweigh the long-term risk and stress of potential IRS challenges.

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For finding tax attorneys who specialize in tax shelters, I'd recommend looking for attorneys who are board-certified in tax law and have specific experience with IRS disputes and tax controversies. The American Bar Association's Section of Taxation maintains directories, and you can also search for attorneys who have published articles or spoken at conferences about tax shelter litigation. Key credentials to look for include: LL.M. in Taxation (advanced tax law degree), experience with Tax Court litigation, and membership in organizations like the American College of Tax Counsel. Many of these attorneys will have worked for the IRS previously, which gives them insight into how the agency approaches these cases. Regarding the statute of limitations - yes, that's exactly the risk. The IRS often takes years to develop enforcement strategies for new tax shelter variations. They might initially accept filings, then later issue guidance or pursue test cases that retroactively challenge similar arrangements. The substantial understatement penalty provision means they can look back 6 years, and if they determine there was any intent to evade taxes, there's no time limit at all. This is why many tax professionals are extremely conservative about aggressive tax strategies - even if something seems legally defensible today, the landscape can change significantly over time.

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Great questions! For finding specialized tax attorneys, look for those with LL.M. degrees in taxation and specific experience with tax controversy/litigation. The American Bar Association's Tax Section maintains directories, and you can search for attorneys who've written articles or spoken at conferences about tax shelter defense. Many larger firms have dedicated tax controversy practices. Also check if they're former IRS attorneys - that experience is invaluable for understanding how the IRS approaches these cases. Ask potential attorneys specifically about their experience with economic substance doctrine cases and whether they've defended clients in similar arrangements. Regarding the statute of limitations - yes, that's exactly right. The IRS can and does develop new enforcement strategies and revisit older transactions. I've seen cases where arrangements that initially seemed to fly under the radar were challenged 4-5 years later when the IRS identified them as part of a broader pattern. The extended limitations period for substantial understatements means you could face scrutiny well beyond the normal 3-year window. This is why the conservative approach of avoiding questionable arrangements altogether is usually the wisest path, even if they seem to offer significant short-term benefits.

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Great questions! For finding tax attorneys who specialize in tax shelters, look for attorneys who are certified as Tax Law Specialists by their state bar (if available) or who have LL.M. degrees in taxation. The American College of Tax Counsel is another good resource for finding experienced tax controversy attorneys. You can also check if they've published articles or spoken at conferences about tax shelter defense - this shows they're actively working in this area. Many larger tax firms have dedicated tax controversy practices that deal specifically with these issues. And yes, your concern about extended limitations is absolutely valid. The IRS continues to refine their enforcement strategies and can challenge arrangements years later. They've also been known to pursue "promoter penalties" against the companies selling these schemes, which can lead them to investigate all participants even if the original returns weren't initially flagged. The safest approach is simply not to participate in arrangements that exist primarily for tax benefits rather than legitimate business purposes. The potential savings rarely justify the ongoing audit risk and legal costs if challenged.

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Great questions! For finding tax attorneys with shelter expertise, look for attorneys who are Board Certified in Tax Law (through the American Bar Association), have LL.M. degrees in taxation, and specifically mention "tax controversy" or "tax shelter defense" in their practice areas. The American College of Tax Counsel is another good credential to look for. You can also check if they've published articles or spoken at conferences about tax shelters - this indicates they're actively working in this specialized area. State bar associations often have tax law sections that can provide referrals to qualified attorneys. Regarding the statute of limitations - yes, that's exactly right. The IRS can and does develop new enforcement strategies and then go back to challenge older returns. They've done this with various schemes over the years. For example, they might initially lack the resources or specific guidance to challenge a particular structure, but then issue new regulations or rulings that clarify their position and audit returns from previous years. The 6-year extended limitation applies if they find a "substantial understatement" (generally 25% or more of correct tax), and as Miguel mentioned, there's no time limit at all if fraud is involved. So even if you file without immediate issues, you could face challenges years later when the IRS catches up to the specific scheme.

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Great questions! For finding tax attorneys who specialize in tax shelters, look for: 1. **Board certification** in tax law from your state bar association 2. **LL.M. in Taxation** degree (Master of Laws in Tax) 3. **Experience with IRS controversies** - specifically mention of defending clients in tax shelter cases 4. **Publications or speaking engagements** on tax shelter topics 5. **Former IRS experience** - attorneys who previously worked in IRS Office of Chief Counsel often have deep insight You can search the American Bar Association's tax section directory or contact your state bar's lawyer referral service and specifically request attorneys with tax shelter defense experience. Regarding the statute of limitations - yes, that's exactly right. The IRS can and does develop new enforcement strategies over time. They might initially lack resources to challenge certain arrangements but then launch coordinated campaigns years later. The *Midco* cases are a perfect example where the IRS went after similar transactions in waves, sometimes 4-5 years after the original returns were filed. This is why the "too good to be true" instinct is so valuable. Even if something technically works initially, you're essentially betting that the IRS won't successfully challenge it later with better resources or refined legal theories.

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Great questions! For finding qualified tax attorneys, look for those who are board-certified in tax law by their state bar association or have an LL.M. in Taxation. The American College of Tax Counsel maintains a directory of experienced tax litigators. You can also check if they've published articles on tax shelter issues or spoken at tax conferences. Regarding the statute of limitations - yes, that's exactly the concern. Even if your initial returns are accepted without audit, the IRS can come back years later if they identify your transaction as part of a broader enforcement initiative. We've seen this with many tax shelter cases where the IRS develops new legal theories or enforcement strategies and then applies them retroactively to similar arrangements. The IRS also maintains "hot lists" of promoters and transaction types they're monitoring. If MyHealth CCM or similar arrangements become a focus area, they could identify participants through various means (bank records, promoter lists, etc.) and audit years of returns. This is why the risk-reward calculation is so important - the potential tax savings rarely justify the long-term audit exposure and potential penalties.

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Great questions! For finding tax attorneys with shelter expertise, look for those who are certified in tax law (LL.M. in Taxation) and specifically advertise experience with IRS disputes or tax shelter defense. The American Bar Association's Tax Section maintains directories, and many large accounting firms have tax attorney partners who handle these issues. Regarding the statute of limitations - yes, that's exactly right and it's one of the scariest aspects of aggressive tax positions. Even if you file and don't get audited initially, the IRS can come back years later, especially if they identify your transaction as part of a broader pattern they're investigating. I've seen cases where taxpayers thought they were "safe" after 3-4 years, only to get hit with audits when the IRS developed new strategies for detecting certain arrangements. The IRS also shares information across years, so if they audit you for one year and find questionable positions, they'll often expand the audit to other years. This is why the "would you do this without tax benefits" test Miguel mentioned is so crucial - it needs to pass that test not just now, but years from now when an auditor is looking back at your motivations.

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Great questions! For finding tax attorneys with tax shelter expertise, look for attorneys who are either: 1. Board certified in tax law (through the American Board of Certification) 2. Former IRS attorneys who worked in the Office of Chief Counsel 3. Attorneys who regularly handle tax controversy and litigation matters 4. Those affiliated with major law firms that have dedicated tax controversy practices You can search the American Bar Association's tax section directory or state bar associations. Also look for attorneys who've published articles on tax shelter issues or spoken at tax conferences. Regarding the statute of limitations - yes, that's exactly the risk. Even if your initial returns are accepted without audit, the IRS can come back later. They're constantly developing new enforcement strategies and identification techniques. What might slip through initially could be caught in a later sweep when they refine their detection methods. The IRS also maintains databases of "promoters" and "participants" in questionable transactions. Once you're in their system as having participated in one arrangement, you become more likely to be scrutinized for other tax positions. It's not worth the long-term exposure for what are often illusory tax benefits.

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Great questions! For finding tax attorneys who specialize in tax shelters, look for attorneys who are board-certified in taxation (either through the American Board of Certification or state bar associations). You can also search the American College of Tax Counsel directory - these are attorneys who specifically handle complex tax controversy and shelter matters. When vetting, ask about their specific experience with abusive tax shelter cases, whether they've handled IRS challenges to similar arrangements, and if they've represented clients in Tax Court for shelter-related disputes. Many general tax attorneys may not have the specialized knowledge needed for these complex arrangements. Regarding the statute of limitations - yes, absolutely. The IRS can and does go back years later, especially as they develop new enforcement tools and databases to identify patterns. They've been particularly aggressive with healthcare-related shelters in recent years. Even if your initial returns aren't questioned, participating in what's later identified as an abusive tax shelter can trigger audits of multiple years' returns, and the penalties can be substantial - sometimes exceeding the original tax savings. This is why the upfront legal analysis is so critical. Better to spend a few thousand on proper legal advice now than potentially face six-figure penalties and legal costs later.

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For finding qualified tax attorneys, look for those who are board certified in tax law (many states offer this certification) or who are Fellows of the American College of Tax Counsel. You can also search the American Bar Association's tax section directory. Experience with IRS controversies and tax shelter litigation is key - ask specifically about their experience defending clients in economic substance doctrine cases. Yes, the extended audit window is a real concern. The IRS can audit up to 6 years later if they find a "substantial understatement" (generally 25% or more of correct tax), and there's no time limit if they determine fraud was involved. Even worse, they're constantly developing new enforcement tools and strategies. What might slip through initially could be caught years later when their detection methods improve. I've seen cases where clients thought they were "safe" after a few years, only to face audits 4-5 years later when the IRS developed new ways to identify these arrangements. The financial and emotional stress of defending against these audits often exceeds any initial tax savings, even when clients ultimately prevail.

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Great questions! For finding qualified tax attorneys, look for those with LL.M. degrees in taxation and specific experience with tax controversy or tax shelter litigation. The American Bar Association's Tax Section maintains directories, and you can also check with your state bar association. Look for attorneys who've handled IRS audits, tax court cases, or written about abusive tax shelters. Yes, the extended statute of limitations is a real concern. Even if you file without immediate issues, the IRS can challenge these arrangements years later as their enforcement strategies evolve. They often identify patterns across multiple taxpayers and then go back to audit everyone who used similar structures. I've seen cases where taxpayers thought they were "safe" after 3-4 years, only to face audits in year 5 or 6. The IRS also has a "Voluntary Correction Program" where they sometimes offer reduced penalties if you come forward before they find you, but that still involves paying back taxes plus interest. The bottom line is that aggressive tax positions create long-term uncertainty that most people underestimate when making these decisions.

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I did sign up with My Health CCM and wished I had not because of the deplorable customer service. It was a 75k investment. Part of the program requires you to watch 100 hours of videos for compliance. I am having trouble with the video platform and have emailed and called the company seven times over the last week, and got one response stating they were forwarding it to the person who could help me. She is the same person who has ghosted me. I finally emailed the owner, expressing my unhappiness and asking to be connected with someone who would actually help me. He only forwarded the email to the same person who has ghosted me. He actually did not respond or apologize after this last email, just forwarded it. She still did not respond, even after it became apparent how unhappy I was, and after the owner forwarded an email to her. She must be family or a friend, because no business owner who truly cares would keep a staff member like this around. If I could get out of this, I would. I paid a company 75k, and they obviously do not care about their clients.

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