Just want to add that capital losses from collectibles can offset capital gains from collectibles. So if you sold some items at a loss and others at a gain, you might end up owing less tax. The hard part is proving what you originally paid if you don't have receipts.

I've been dealing with this exact situation and wanted to share what I learned from my research and talking to a tax professional. The key thing to understand is that there's a difference between selling personal items at a loss (which most garage sale items are) versus selling collectibles that have appreciated in value. For your garage sale items, if you're selling personal belongings for less than what you paid, there's generally no tax consequence. The IRS considers these personal losses, which aren't deductible but also aren't taxable income. For collectibles that have increased in value, you do need to report the gains. The tricky part about not having receipts is real, but the IRS allows "reasonable estimates" of your cost basis. You can research what similar items sold for when you originally bought them using price guides, auction records, or inflation calculators. One thing that surprised me: collectibles are taxed differently than stocks - they're subject to a maximum 28% rate rather than the lower long-term capital gains rates. So it's worth tracking these separately. As for whether the IRS will "come after you" for small amounts - while technically all income should be reported, enforcement resources are typically focused on larger discrepancies. That said, with new 1099-K reporting requirements lowering to $600 in 2025, there will be more paper trails for online sales.

I'm pretty sure theres a different form u need to use when selling a business asset vs a personal one? Is it like form 4797 or somethin? My buddy who does real estate told me you gotta split the sale between business/personal somehow

This is such a common problem for real estate agents! I went through something similar with my 2017 Camry that I used for showings and personal driving. One thing that really helped me was creating a spreadsheet to track down all my depreciation across the years - I went through each tax return and pulled out every vehicle-related deduction. Don't forget that if you used the standard mileage method, you need to look at the depreciation component for each year (it changes annually). For 2018 it was about 25 cents per mile, 2019 was 26 cents, etc. The IRS publishes these breakdowns in their annual mileage rate announcements. Also, make sure you're consistent with your business use percentage when you calculate the sale. If you've been all over the map with percentages (like 65% some years, 80% others), you might want to use an average or be prepared to explain the variation if questioned. The key is having good records to support whatever percentage you use for the final calculation. One last tip - if your total depreciation taken exceeds what the car actually depreciated in value, you might have some depreciation recapture even if you're selling at a "loss" from your original purchase price. This catches a lot of people off guard!

You might also want to check if you need to make an estimated tax payment this quarter rather than waiting until tax time. If you're normally a W-2 employee who gets refunds, you're probably fine waiting. But if this pushes your tax due over $1k for the year beyond what's being withheld, you might need to make an estimated payment to avoid an underpayment penalty.

Congratulations on your win! You've gotten some great advice here already. Just to add a bit more clarity - yes, you absolutely need to report this as "Other Income" on your tax return regardless of whether you receive a W-2G form or not. One thing I'd suggest is opening a separate savings account and immediately putting aside 25-30% of your winnings ($1,200-$1,440) for taxes. This covers both federal and state obligations and gives you a small buffer. It's much easier to do this now while you have the full amount than to scramble for tax money next April. Also, start keeping a simple log of any gambling activities for the rest of the year - both wins and losses. Even if you just buy a few lottery tickets or play bingo, track it all. If you itemize deductions, those losses can offset your winnings dollar-for-dollar up to the amount you won. The IRS considers all gambling winnings taxable income from dollar one, so there's no minimum threshold for reporting requirements on your end, even though there are thresholds for when organizations must issue forms to you.

This situation is more common than you might think, and you're smart to address it now rather than letting it continue. Based on what you've described - especially the 83(b) election filing - you almost certainly should be treated as a partner rather than an employee for tax purposes. The key issue is that when you receive profit interests in an LLC, you become a partner in the partnership, which fundamentally changes your tax status. Partners don't receive W-2s or have taxes withheld - instead, they receive K-1s and typically make quarterly estimated payments. Here's what I'd recommend for your immediate situation: 1. **Don't file yet using just the W-2** - this could lock in the incorrect treatment and make corrections more complicated later. 2. **Get professional help first** - find a CPA who specializes in partnership taxation. This isn't standard tax prep territory, so make sure they have specific experience with profit interests and partnership issues. 3. **Gather all your documents** - profit interest agreement, 83(b) election filing confirmation, any other equity-related paperwork. Your tax professional will need these to assess your situation properly. 4. **Talk to your employer after you understand the issue** - approach them with solutions, not just problems. They probably don't realize the tax implications and will appreciate guidance on how to fix it. Regarding your future plans to potentially give back the units or move abroad - both are definitely possible, but the international tax implications of being a US partnership partner while living abroad can be quite complex. Address the current year first, then work with your professional to plan the best long-term strategy. The good news is that since taxes were being withheld and paid, you're not in a "no taxes paid" situation, which is what the IRS really cares about. This is fixable with the right professional guidance.

Yes, absolutely mention "profit interests" specifically when calling tax professionals! This is a very particular area of partnership taxation, and you want someone who has direct experience with Section 83(b) elections, profit interest valuations, and the employee-to-partner transition issues. When you call, you can say something like: "I received profit interests in my LLC employer, filed an 83(b) election, but I'm still being treated as a W-2 employee instead of receiving a K-1. I need help determining my correct tax status and fixing any compliance issues." A specialist in this area will immediately understand your situation and should be able to discuss the common approaches for resolving it. If they seem unfamiliar with profit interests or start asking basic questions about what they are, keep looking. Also, don't lose sleep over this! The IRS sees these situations regularly - small companies frequently mishandle the tax implications of equity compensation. The fact that you're proactively addressing it and that taxes have been getting paid puts you in a much better position than someone who just ignored it completely. You're taking exactly the right steps by getting professional guidance before making any filing decisions. This is definitely in the "complicated but totally fixable" category, not the "irreversibly screwed up" category!

This thread has been incredibly helpful! I'm in a very similar situation - divorced in 2015, modified the agreement in 2024 with no mention of tax implications. After reading everyone's experiences, I feel much more confident about continuing to take the deduction. What really stands out to me is how consistent everyone's advice has been: if the modification doesn't explicitly state that the new tax rules apply, then the original pre-2019 treatment continues. The IRS seems to have written this rule pretty clearly - they require express language, not implied or assumed changes. For anyone else in this situation, I'd recommend: 1. Keep copies of both your original divorce decree AND the modification 2. Make sure your ex-spouse understands they still need to report the payments as income 3. Consider adding protective language to any future modifications (like @Rudy Cenizo suggested) 4. Keep detailed records of all payments It's frustrating that the IRS publications aren't clearer about this, but based on everyone's real-world experiences here, it seems like we're interpreting the law correctly. Thanks to everyone who shared their stories - it's so much more helpful than trying to decode tax publications alone!

This entire discussion has been so valuable! As someone who went through a similar situation with a 2014 divorce agreement modified in 2023, I can confirm that the consensus here is absolutely correct. The key really is whether your modification contains explicit language about adopting the new tax rules. What I'd add from my experience is that it's worth having a conversation with your ex-spouse about this before tax season to make sure you're both on the same page. In my case, my ex had heard from friends that "alimony isn't taxable anymore" and stopped reporting it as income in 2023. This created a mismatch that could have triggered issues for both of us. I had to show them the actual tax code and explain that for our pre-2019 agreement (even with modifications), the old rules still apply unless specifically changed. Now we both file consistently - I deduct, they report as income - and everything works smoothly. The bottom line for anyone in this situation: silence in your modification is your friend, but communication with your ex-spouse is essential to avoid filing inconsistencies that draw IRS attention.