Based on your description of My Health CCM's pitch, this has all the hallmarks of an abusive tax shelter. The combination of creating a special purpose LLC solely for tax benefits, making a large "investment" in software licenses, and promises of dramatic tax savings should be raising every red flag. The IRS has been cracking down hard on these types of schemes. They often involve overvalued intangible assets (like software licenses) to create artificial losses that get passed through to your personal return. Even if the promoters claim it's "legal," the IRS can disallow the deductions under the economic substance doctrine. I'd strongly recommend staying far away from My Health CCM. If you're looking to legitimately reduce your tax burden, consider working with a reputable CPA or tax attorney who can help you implement proven strategies like maximizing retirement contributions, proper business expense documentation, or legitimate business structures that serve actual economic purposes beyond tax avoidance. Remember: if someone is cold-calling you with a "tax strategy" that sounds too good to be true, it probably is. Legitimate tax planning doesn't typically require you to invest six figures in questionable software licenses.

As someone who's been through multiple IRS audits, I can tell you that My Health CCM's pitch hits every single warning sign for what the IRS calls "abusive tax avoidance transactions." The fact that they're pushing you to create a special purpose LLC specifically for tax benefits rather than legitimate business operations is a massive red flag. I learned the hard way that the IRS doesn't care what promoters claim is "legal" - they look at the economic substance of the transaction. If you're paying $130k for software licenses that you'll never actually use in a real business, that's exactly the kind of artificial loss creation they go after aggressively. The penalties aren't just financial either. These schemes can put you on the IRS's radar permanently, making you a target for future audits. I'd recommend getting a second opinion from a licensed tax professional who has no financial interest in selling you this "strategy." Most legitimate CPAs will tell you to run from anything that sounds like what you've described. Trust your gut - if it sounds too good to be true, it almost certainly is. There are plenty of legitimate ways to reduce your tax burden without risking your financial future on schemes like this.

Has anyone tried using the IRS Modernized e-File (MeF) system through a tax software like ProSeries or Lacerte? You can usually e-file business extensions through them if you already subscribe for other business tax prep.

I'm in a similar situation with my LLC extension and found that while the IRS doesn't offer free direct e-filing for business forms like 7004, there are a few workarounds worth considering. One option is to check if your state has any partnerships with e-file providers that might offer discounted rates for extensions. Some states negotiate bulk pricing that gets passed on to taxpayers. Also, if you're comfortable with paper filing as AstroAce mentioned, you can actually track your mailed return through the IRS website using their "Where's My Amended Return?" tool (though it takes a few weeks to show up in their system). It's not as immediate as e-filing confirmation, but it does give you eventual verification that they received and processed your extension. For what it's worth, I ended up biting the bullet and paying the $35 fee last year because the peace of mind from instant confirmation was worth it to me, especially since missing the extension deadline would have cost way more in penalties.

I'm new to this community and this has been such an informative thread! Everyone's really covered the tax side thoroughly - you'll be fine as long as your friend sends the $490 as a personal payment for the exact reimbursement amount. But wow, I had no idea employee discount policies were so strict! Reading all these stories about people getting fired for gaming console purchases with their discounts is honestly shocking. It sounds like these high-value electronics are specifically flagged in retailer systems because they're popular resale items. Given that you mentioned money is already tight, the math here really doesn't work out in your favor. Risking your job and losing that 30% discount permanently over helping your friend save $200 just isn't worth it. That discount is probably worth thousands to you over time for your own purchases. Have you considered helping your friend find other legitimate ways to save? Maybe price matching policies, waiting for holiday sales, or checking if there are any student/military discounts he might qualify for? Sometimes the best way to help a friend is protecting yourself from unnecessary risks so you can be there for them in the long run. Your financial stability has to come first, especially when you're already dealing with tight finances!

I'm new to this community and wanted to add my thoughts after reading through this really helpful discussion! Everyone's done a great job explaining the tax side - you're totally safe there as long as your friend sends exactly $490 as a personal payment and you keep your receipt. But honestly, I'm really concerned about all these warnings regarding employee discount policies. I had no idea retailers monitored high-value purchases so closely! The stories about people getting fired specifically for gaming console purchases are eye-opening and pretty scary. Since you mentioned you're already tight on money, this feels like a huge risk for a relatively small reward. Losing your job and that 30% discount permanently could cost you thousands over time, way more than the $200 your friend would save. That discount is probably one of the most valuable benefits of your retail job. Maybe you could help your friend explore other options? Price matching, waiting for Black Friday sales, checking for student discounts, or even store credit card signup bonuses might get him a deal without putting your employment at risk. Your financial security has to come first, especially when money's already tight. A good friend would totally understand if you explained the policy risks - they wouldn't want you jeopardizing your livelihood for their savings!

I had to call that number last month. They asked questions about my mortgage, previous addresses, and credit cards I have. Took about 20 minutes once I got through to someone. Is that similar to what others experienced? Did they also ask about loan amounts or just the existence of accounts?

Just wanted to add my recent experience - called 800-830-5084 last week after receiving a 5071C letter. The security questions were pretty thorough - they asked about my previous addresses going back 5 years, specific loan amounts (not just existence), and even asked about a credit card I had closed 2 years ago. The whole verification took about 25 minutes once connected, and they processed my return immediately. One tip: have your Social Security statement handy if you can access it online. They asked about my reported wages from 2 years ago which I wouldn't have remembered otherwise. The agent was very patient and professional throughout the process. For those asking about wait times - I called at 8:30 AM EST on a Tuesday and waited about 55 minutes, which seems pretty typical based on what others are reporting here.

This is a complex situation that really highlights the importance of understanding trust tax elections before making these transfers. One thing I haven't seen mentioned yet is the potential for making a Section 645 election if your grandparents' trust qualifies. If this is a qualified revocable trust that became irrevocable upon your grandparents' death (or if they're still alive but incapacitated), the trustee might be able to elect to treat the trust as part of the estate for income tax purposes during the first two years. This could potentially preserve access to certain individual tax benefits. Also, even if the trust doesn't qualify for the capital gains exclusion, don't forget that trusts get their own capital gains tax brackets. The rates can be quite high (up to 20% plus the 3.8% net investment income tax), but proper timing of the sale and potentially distributing some gains to beneficiaries in lower tax brackets could help minimize the overall tax impact. I'd strongly recommend getting a comprehensive analysis from a tax professional who specializes in trust taxation before proceeding with the sale. The potential tax savings from getting this right could easily justify the consultation cost.

This thread has been incredibly helpful! I'm dealing with a similar situation with my elderly parents who put their home in an irrevocable trust about 5 years ago. Based on what I'm reading here, it sounds like the key is determining whether their trust maintains grantor trust status. From the discussion, it seems like there are a few good options for getting clarity: consulting with the original estate planning attorney, using services like taxr.ai for professional analysis, or even getting through to the IRS directly (though that last one sounds challenging without help like Claimyr). One question I have - if the trust IS determined to be a grantor trust and they can claim the exclusion, do they report the sale on their personal tax return (Form 1040) or does it still need to go through the trust's return? I want to make sure we handle the reporting correctly to avoid any red flags with the IRS. Thanks to everyone who shared their experiences - this is exactly the kind of real-world insight that's hard to find elsewhere!