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Can somone explain why the government allows businesses to deduct losses but not individual gamblers? If I start an LLC for my sports betting, could I then deduct the losses?
Creating an LLC won't help you deduct gambling losses against ordinary income. The IRS specifically classifies gambling as a personal activity, not a business, unless you can prove you're a "professional gambler." To be considered a professional gambler, you must demonstrate that you approach gambling as a business with the primary purpose of making a profit, not entertainment. This includes maintaining complete records, having expertise, devoting significant time to gambling activities, and showing a history of profitability. It's an extremely high bar that few people meet. Even professional gamblers face restrictions - their losses can only offset gambling income, not other types of income. Additionally, attempting to create an LLC just to reclassify personal gambling as a business could potentially be viewed as tax avoidance by the IRS.
I've been following this discussion and wanted to add something important that hasn't been mentioned yet - the timing of when you report gambling winnings and losses. If you're planning to make that $3,800 bet next month, remember that any winnings or losses will be reportable on your 2025 tax return (due April 2026), not your current 2024 return. This might affect your tax planning strategy. Also, if you do win and receive a Form W-2G from the sportsbook (which you typically get for winnings over $600 that are at least 300 times your wager), the IRS already knows about your winnings. Make sure you report them even if you don't receive a tax form - the threshold for reporting gambling income to the IRS is actually lower than what triggers a W-2G. One more thing - if you're in a state where sports betting winnings are subject to state taxes, remember that the rules for deducting gambling losses at the state level can be completely different from federal rules. Some states don't allow gambling loss deductions at all, even if you itemize federally.
This is really helpful timing information! I hadn't thought about the fact that a bet made next month would affect my 2025 taxes, not 2024. That actually gives me more time to plan around it. Quick question about the W-2G threshold - you mentioned winnings over $600 that are at least 300 times the wager. For a $3,800 bet with a potential $3,150 profit, would that trigger a W-2G? And does the sportsbook automatically withhold taxes when they issue one, or do I need to set money aside myself for tax time? Also, regarding state taxes - I'm in New Jersey where sports betting is legal. Do you know if NJ follows the federal rules for gambling loss deductions, or do they have their own restrictions?
Can someone explain why this even matters? If it's your S-Corp and all the money flows to you either way, why does the IRS care how you classify it?
It matters because of employment taxes. S-Corp distributions aren't subject to self-employment tax (Social Security and Medicare), but wages are. At 15.3% combined (employer + employee portions), the tax difference can be huge. This is exactly why the IRS scrutinizes S-Corp compensation - they want to make sure business owners aren't avoiding employment taxes by taking artificially low salaries and large distributions. They're particularly focused on professional service businesses like law, accounting, medicine, etc. where the owner's personal services generate most of the income.
The reasonable compensation analysis for your situation is complex, but I'd strongly recommend documenting your decision process thoroughly. As others have mentioned, $168,600 is almost certainly too low for a $5M law practice. One approach I've seen work well is to break down your compensation into components: (1) what you'd pay an attorney with your experience to handle the legal work, (2) what you'd pay someone to manage a business of this size, and (3) any premium for specialized expertise or client relationships you bring. You might also consider a gradual approach - if you've been taking minimal salary historically, the IRS may be more understanding of a phased increase to reasonable levels over 2-3 years rather than a sudden jump. This shows good faith effort to comply while managing cash flow. Whatever number you settle on, make sure you can justify it with market data and keep detailed records. The IRS burden is to prove compensation is unreasonable, but you want to make their job as difficult as possible with solid documentation.
This is really helpful advice about the phased approach. I'm curious about the documentation aspect - what kind of market data sources are typically most convincing to the IRS? Are salary surveys from legal publications sufficient, or do they prefer more formal compensation studies? And how detailed do the records need to be regarding the breakdown between legal work vs. business management activities?
Has anyone used one of those DIY cost segregation software programs? I've seen a few advertised that supposedly let you do your own study for a few hundred bucks. Wondering if those are legitimate or just asking for trouble.
I tried one of those software options last year for my triplex. It was basically just a glorified spreadsheet that didn't really provide any defensible documentation. My tax guy told me it wouldn't hold up in an audit. I ended up just doing regular depreciation instead. Not worth the risk.
Thanks for sharing your experience. That confirms my suspicions. Sounds like there's no real middle ground between doing it properly with professional help and taking too much risk with a DIY approach.
I was in a similar situation with my rental duplex last year. My CPA initially suggested the case law approach, but after reading all these responses, I decided to go with a hybrid solution and used the taxr.ai service that Ella mentioned. What really sold me was that it gave me professional-level documentation without the full engineering study cost. The report they generated was detailed enough that my CPA was comfortable filing it, and it included specific references to the methodology they used for categorizing different property components. For your $875K property, you're probably looking at significant potential savings. I'd suggest at least getting a quote from taxr.ai to compare against what a full engineering study would cost. In my case, the additional first-year deductions more than paid for the service cost, and I feel much more confident about audit defense than I would have with just the case law approach. The peace of mind was worth it for me - especially since rental property depreciation can be scrutinized more closely by the IRS.
This is really helpful perspective! I'm actually leaning towards checking out the taxr.ai option after reading all these experiences. It sounds like it provides a good middle ground between the risky case law approach and paying for a full engineering study. @d76823c86837 How long did the whole process take from start to finish? And did you need to provide a lot of detailed information about your property, or was it pretty straightforward? I'm also curious if anyone has compared the taxr.ai results directly against a traditional engineering study to see how close the allocations were. For an $875K property, even a small difference in allocation percentages could mean thousands in tax implications.
Last year my friend with international income had a similar situation - blank transcript for weeks with cycle 05. When he finally called after 8 weeks, turns out his return had been selected for a "compliance review" because of foreign income reporting. They never sent a letter! The IRS agent told him international returns are frequently held for additional verification without notification. Not saying that's happening to you, but might be worth calling if you don't see movement by mid-March.
I'm going through the exact same thing! Filed January 28th, cycle 05, completely blank transcript, and that March 3rd "as of" date. It's so frustrating not knowing what's happening behind the scenes. What's really getting to me is that I carefully reported all my foreign income using Form 8938 and FBAR, thinking I was being thorough, but now I'm wondering if that's exactly why it's taking so long. Has anyone else noticed if having foreign accounts or income automatically triggers these extended reviews? I've been checking my transcript every Thursday night (since that's when cycle 05 updates) and literally nothing changes. At least knowing others are in the same boat makes me feel less alone in this waiting game! š Thanks for posting this - sometimes you need to know you're not the only one dealing with IRS mysteries!
Mei Wong
Great thread! I'm going through this process right now with my first rental property. One thing I learned that might help others - make sure to factor in your state taxes too when calculating potential savings. I'm in California with high state income taxes, so my effective tax rate on the accelerated depreciation is actually higher than just the federal rate, which made the numbers work even better. Also, if you're planning to do multiple properties, some companies offer package deals that can bring the per-property cost down significantly. I'm getting quotes for doing 4 properties at once and the cost per study drops from about $5K each to around $3K each when bundled. One question for those who've done this - do you typically do the cost segregation in the same year you purchase the property, or wait until the following tax year? I closed in December and wondering if there's any advantage to timing it one way or the other.
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Mila Walker
ā¢Great point about state taxes! For timing, there's actually no difference whether you do it in the purchase year or later - you can still claim all the accelerated depreciation in whatever year you complete the study through that catch-up provision mentioned earlier. I did mine two years after purchase and got the full benefit. However, if you closed in December, you might want to consider whether doing it this tax year makes sense based on your current income situation. If you have a high-income year, the deductions are more valuable. But if you expect higher income next year, you could wait. The flexibility is one of the nice things about cost segregation - you're not locked into doing it immediately after purchase. Those package deals sound great! I wish I'd known about bundling when I did my properties separately. Definitely something for others to keep in mind if they have multiple properties.
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Giovanni Martello
This is incredibly helpful! I'm a tax professional and see so many rental property owners missing out on cost segregation benefits. A few additional points that might help: **Documentation is key** - Start gathering all your purchase documents, renovation receipts, and any property improvement records NOW. The more detailed documentation you have, the better the cost segregation study will be. Even small improvements like new flooring, fixtures, or landscaping can often be reclassified. **Consider bonus depreciation** - For 2024, you can still take 80% bonus depreciation on qualifying property identified through cost segregation (drops to 60% in 2025). This means even MORE immediate tax benefits on top of the accelerated depreciation schedules. **Don't forget about Section 199A** - If you qualify for the 20% QBI deduction on rental income, the depreciation from cost segregation can actually help you maximize this benefit by reducing your taxable rental income while potentially keeping you in the qualifying income ranges. For those asking about smaller properties - I've seen studies pencil out on properties as small as $200K, especially if there have been significant renovations or if the property has unique features like pools, extensive landscaping, or high-end finishes that can be segregated into shorter depreciation lives. The key is finding the right professional who understands both the engineering side AND the tax implications. Not all cost segregation companies are created equal!
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William Rivera
ā¢This is exactly the kind of comprehensive advice I was hoping to find! The bonus depreciation point is huge - I hadn't realized it was still at 80% for 2024. That makes the timing even more compelling for getting this done before year-end. Quick question on the Section 199A angle - I'm currently above the income threshold where QBI starts phasing out. Would the increased depreciation deductions from cost segregation potentially bring me back into the range where I could claim the full 20% deduction? If so, that's like getting a double tax benefit. Also appreciate the point about documentation. I've been pretty good about keeping renovation receipts but definitely have some gaps from earlier years. Would it be worth trying to reconstruct some of those records (like getting contractor invoices from previous work) or do most cost segregation studies work fine with just the major documentation?
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