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I'm a wealth management advisor who works with several HNW real estate investors. Beyond just attorneys and CPAs, make sure your clients have a comprehensive team that includes: 1. A real estate-focused wealth strategist who can coordinate between all the specialists 2. An estate planning attorney (separate from the tax attorney) 3. A CPA who specifically handles real estate investments 4. A cost segregation specialist to maximize depreciation benefits The biggest mistake I see with new real estate investors is treating properties as isolated investments rather than creating a cohesive strategy across their entire portfolio. Each new acquisition should be evaluated not just on its own merits but how it affects their overall tax situation.
How often should HNW clients have their tax strategy reviewed? Is it something that needs adjustment every year or is a good strategy supposed to last for several years? And does having multiple properties across different states complicate things significantly?
Tax strategies should be reviewed quarterly at minimum, with a comprehensive overhaul annually. Tax laws change frequently, and as a portfolio grows, different strategies become available. What works for 3-4 properties often becomes suboptimal at 10-12 properties. Multi-state portfolios absolutely complicate matters and often require state-specific expertise. Each state has different tax treatments for out-of-state owners, and some entity structures that work well in one state can create unnecessary tax burdens in others. This is especially true with states like California, New York, and Texas, which have very different approaches to taxation.
Don't forget about DSTs (Delaware Statutory Trusts) as an option for HNW real estate investors! I've seen several families use these effectively as part of their 1031 exchange strategy, especially when they want to diversify but stay in real estate. The real magic happens when you combine entity structuring with proper timing of recognizing income and losses. We've had clients save literally millions by properly sequencing when they sell properties and when they accelerate expenses.
DSTs have serious downsides though. You lose operational control, returns are often lower than direct ownership, and the fees can be substantial. Plus, you're locked in for the duration with very limited liquidity. They're not always the best choice for active investors who want to grow their portfolio.
I think everyone is overreacting to this news. I'm a small business attorney who works with dozens of clients affected by the CTA. Here's the real deal: this enforcement pause is almost certainly temporary. The Treasury Department is likely responding to legal challenges, but once those are resolved, enforcement will resume. My advice to clients remains unchanged: prepare your beneficial ownership information now so you're ready to file when needed. The requirements themselves haven't been eliminated, just the enforcement mechanism. For most legitimate small businesses, the reporting isn't actually that burdensome - it's identifying the beneficial owners (those with 25%+ ownership or substantial control) and providing basic information about them. Don't use this pause as an excuse to ignore your obligations completely, or you might find yourself scrambling when enforcement suddenly resumes.
What about companies formed in 2023? I thought we had different deadlines than older companies. Does this pause affect all businesses the same way?
Companies formed in 2023 fall under the "existing entities" category, which originally had until January 1, 2025 to file their initial reports. Companies formed in 2024 have 90 days from formation to file. The enforcement pause affects all businesses subject to the CTA equally - regardless of when they were formed. However, it's important to note that the technical legal requirement still exists for all applicable businesses, even though there's no enforcement mechanism currently in place. My recommendation remains to prepare your information so you're ready when enforcement resumes, which it almost certainly will.
Does anyone know if this affects companies that already filed their beneficial ownership information? I submitted mine in January when the requirements first went into effect. Did I waste my time? Should I be worried about the information being in their system now that they're not enforcing the rule?
You didn't waste your time. If anything, you're ahead of the game. The database still exists and your information is properly recorded. When enforcement resumes (which most experts think it will), you won't have to scramble like everyone else.
I got behind on taxes for about 4 years while dealing with severe depression. What really helped me was contacting the Taxpayer Advocate Service - it's a free, independent organization within the IRS that helps people resolve tax problems. They assigned me an advocate who helped me through the whole process. For the ADHD aspect, bring documentation from your doctor when you speak with tax professionals. While there's no specific program for neurodivergent folks, medical issues (including mental health) can sometimes qualify for penalty abatement under "reasonable cause" if you can show it directly impacted your ability to comply with tax obligations.
I've never heard of the Taxpayer Advocate Service. Do they help with complicated situations involving multiple years and different income sources? Also, do they help negotiate payment plans or is that a separate process?
Yes, they absolutely help with complicated multi-year situations - that's actually their specialty. My case involved W2 income, freelance work, and some investment income across several years. They're particularly helpful when your case has special circumstances or when you've tried to resolve issues through normal IRS channels without success. The advocate can help with the entire process including setting up payment plans and exploring options like Offers in Compromise if you can't pay the full amount. They'll look at your financial situation holistically and recommend the best approach. They can even request holds on collection activities while you're working with them. To contact them, call 1-877-777-4778 or find your local office on the IRS website.
One thing nobody's mentioned is that you might actually be owed refunds for some of those years! I was in a similar boat (5 years unfiled) and when I finally did my taxes, I discovered I was due refunds for 2 of those years because of over-withholding from my W2 job. The catch is you only have 3 years to claim refunds, so some might be gone forever, but it's worth checking. Also look into IRS Free File if your income is under $73,000 - you can file current and some prior year returns for free with guided software.
This is a really good point. My brother thought he'd owe thousands, but ended up getting about $1,500 back because his W2 withholding more than covered what he owed from his side gig. Don't assume you'll owe until you run the numbers!
For your tutoring situation, make sure you also track your mileage if you drove to tutoring sessions! I tutor for three different companies and track everything in a simple spreadsheet - date, student, amount paid, and miles driven. The standard mileage deduction is pretty generous (62.5 cents per mile for 2022) and can really add up even if you're not driving far. Just tracking my 5-mile drives to the library twice a week saved me almost $200 in taxes last year.
Oh that's super helpful - I didn't even think about mileage! I was taking the campus shuttle to most sessions but sometimes I did drive to off-campus locations. Do you need any special documentation for mileage or just a log?
A simple log is enough! Just note the date, starting location, ending location, purpose of trip (tutoring), and miles driven. I keep mine in a notes app on my phone so I can update it right after each session. You don't need anything fancy - just enough detail that you could explain it if questioned. Only track the miles specifically for tutoring though, not your regular commute to campus or personal trips.
Don't forget that as an independent contractor, you'll also need to pay self-employment tax (15.3%) on your tutoring income if you made more than $400, even though you won't get a 1099! I made this mistake my first year tutoring and got hit with an unexpected tax bill.
Yep, that self-employment tax is brutal! But remember you can deduct half of it on your 1040, which helps a little bit. Schedule SE calculates this automatically.
Kiara Fisherman
Your mom should pull any files for clients who claimed EITC, CTC, AOTC, or HOH status from the last year. Those are the typical targets for due diligence visits. Make sure she has Form 8867 (Paid Preparer's Due Diligence Checklist) for each of those returns with all questions answered. The IRS is checking if she's doing the required verification before claiming these credits.
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Dylan Baskin
ā¢That's really helpful - I'll make sure she focuses on those specific credits first. Is there anything else she should have ready besides the Form 8867 and supporting documentation?
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Kiara Fisherman
ā¢She should also have her written due diligence procedures available - even if it's just a basic checklist of what she asks clients and what documents she collects. The IRS wants to see that she has a consistent process. Also have her review her records for any cases where she might have rejected claiming a credit when a client couldn't provide adequate documentation. This shows the IRS she's not just rubber-stamping everything. And remind her that they'll likely ask questions about her knowledge of the eligibility requirements for these credits, so a quick review of the current rules wouldn't hurt.
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Liam Cortez
As a preparer who went through this, the best advice is DON'T PANIC! The consequences really depend on what they find. Minor issues usually just mean recommendations. If they find significant failures (like claiming credits without proper documentation), penalties start around $540 per failure. But its usually per category of failure, not per mistake on each return. My visit took about 3 hours total.
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Savannah Vin
ā¢Is there a way to know which returns they'll select? My practice got notice of a visit too and I'm freaking out trying to organize everything!
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