This is really helpful to see everyone's experiences with the QBI deduction! I'm in a similar boat - been doing some freelance consulting work on the side and wasn't sure about QBI eligibility. One thing I'd add for anyone considering amending previous returns: make sure to check if you filed Schedule C for your freelance income in those prior years. The QBI deduction is tied to business income reported on Schedule C (or other business forms), so if you just reported your 1099-NEC as "other income" without filing Schedule C, you might need to correct that first before claiming QBI. Also, don't forget that you can only go back 3 years to amend, so if you had qualifying freelance income in 2020 or earlier, that window has closed. But for 2021-2023 returns, it's definitely worth looking into if you missed this deduction!

This thread has been incredibly helpful! I'm a freelance web developer who's been missing out on the QBI deduction for years because I thought it was only for "real businesses." After reading through everyone's experiences, I realized I've been leaving money on the table. I receive multiple 1099-NECs each year and always file Schedule C, but my tax software never prompted me about QBI. I'm definitely going to look into amending my 2022 and 2023 returns - with about $15k in freelance income each year, the 20% deduction could mean significant refunds. One question for the group: if you're amending multiple years, is it better to file all the amendments at once or space them out? I'm worried about triggering any red flags with the IRS by suddenly claiming deductions I missed for multiple years.

This is such a helpful discussion! I'm in a similar situation with my mountain cabin rental and have been going back and forth on this exact issue. One thing I haven't seen mentioned yet is the impact of local regulations on this classification. In my area, short-term rentals are required to have 24/7 on-site management response, daily safety inspections, and we must provide certain amenities by law. These regulatory requirements essentially force us to provide what could be considered "substantial services." I'm wondering if anyone has had success using local STR regulations as supporting documentation for self-employment classification? It seems like if the government is requiring you to provide hotel-like services, that could strengthen the argument that you're running an active business rather than just renting property. Also, for those tracking time - I've found that breaking down services into categories helps: guest communication, property maintenance, cleaning/turnover, guest services (recommendations, problem-solving), and regulatory compliance. The IRS seems to view guest-focused services differently than property maintenance when evaluating the substantial services test.

This is exactly the kind of thorny tax issue that keeps me up at night! I've been running a small B&B-style operation (converted garage apartment) for about 18 months and struggling with the same classification question. What's particularly frustrating is that the IRS guidance feels so vague on what constitutes "substantial services." I provide daily housekeeping, prepare continental breakfast, offer laundry service, and even do airport pickups for guests - but my accountant is still hesitant to classify it as self-employment income. The social security credits are a big deal for me since I'm self-employed and this is my primary income source. Has anyone had success getting a private letter ruling from the IRS on this specific issue? I know they're expensive and time-consuming, but it might be worth it for the certainty. Also wondering about the passive activity loss rules - if I do claim this as self-employment income on Schedule C, am I potentially losing out on any rental loss deductions I could take on Schedule E? Seems like there might be trade-offs beyond just the social security credits to consider.

I'm glad to see someone being responsible about both their gambling habits and tax obligations! Your $150 net winnings situation is pretty common, and you're smart to ask about it upfront. Just to reinforce what others have said - yes, you'll need to report all your gambling winnings as income, not just the $150 net. So if you won $500 total but lost $350, you report the full $500. The losses can potentially be deducted if you itemize, but for most people with smaller gambling activity, taking the standard deduction and paying tax on the gross winnings ends up being simpler. Since you're planning to quit while ahead, make sure to download your complete betting histories from all platforms before you close those accounts. Even though $150 seems small, having proper documentation protects you if there are ever any questions down the line. The actual tax you'll owe on this is probably going to be pretty minimal - maybe $30-50 depending on your bracket. Definitely worth being compliant for that small amount rather than risking penalties later. Good luck with your tax filing, and congratulations on walking away with a profit!

I'm in a very similar situation - made about $180 from sports betting this year and was also wondering about reporting requirements. Reading through all these responses has been incredibly helpful! The key takeaway for me is that it's not just about the net profit ($150 in your case), but you need to report ALL your individual winning bets as income. So if you actually won $600 total but lost $450 to get to that $150 net, you're reporting $600 as gambling income. One thing I'd suggest is using the search function on your betting apps to filter by "winning bets" or "settled wins" - this made it much easier for me to calculate my total winnings versus trying to go through every single transaction. Most platforms like DraftKings and FanDuel have pretty good filtering tools in their transaction history sections. Also wanted to say good for you on recognizing when to step away! The fact that you're being proactive about the tax implications shows you're approaching this responsibly. The actual tax hit on amounts like ours really isn't that bad - probably less than what we'd spend on dinner out. Worth being compliant and having peace of mind.

Quick question for the group - does anyone use any specific tax software that handles day trading well? I tried using TurboTax last year and it was a nightmare with all my trades!

This is such a common confusion for new traders! I went through the exact same thing when I started trading full-time. The key thing to understand is that your LLC structure doesn't change the fundamental tax treatment of trading profits - they're still considered capital gains, not business income subject to self-employment tax. However, I'd strongly recommend getting professional help to navigate this properly. As others mentioned, while your trading profits won't be subject to SE tax, you need to be careful about separating any other business activities (like if you start offering trading courses or signals). Also, make sure you're tracking all your trading-related expenses properly - home office, equipment, data feeds, etc. can all be deductible. One thing to keep in mind for next year: if you do qualify for TTS, you'll want to make that election by the filing deadline. It won't change the SE tax situation, but it will give you better expense deductions and allow you to deduct trading losses above the $3k capital loss limit. Definitely start making quarterly estimated payments based on your expected annual profits - the IRS doesn't care that you're not paying SE tax, they still want their income tax!

Don't forget about the look-back period! Medicaid will scrutinize any large deposits or withdrawals in the last 5 years, so be ready to explain those if they appear on the tax forms. My mom's application got delayed because she had capital gains from selling her house, and even though it was an exempt asset, we still had to provide additional documentation.

Another thing to keep in mind - some states have specific Medicaid application checklists that tell you exactly which tax forms they need. I wish I had known this earlier! When I was going through this process with my father last year, I spent weeks trying to figure out what to include. Then I discovered our state's Medicaid website had a downloadable checklist specifically for long-term care applications that broke down exactly which tax documents were required. It saved me from both over-submitting (like including every single TurboTax worksheet) and under-submitting (I almost forgot to include his 1099-R forms for pension distributions). The checklist even had little boxes to check off as you gathered each document. If your state has something similar, it might be worth looking for before you start printing everything. Some states even have different requirements depending on whether it's for nursing home care vs. home-based care services.