I'm confused about one thing - if the apartment is outside the US, don't you have to report it on FBAR and Form 8938 regardless of whether it's rental or personal? My accountant told me all foreign properties need to be disclosed even if they don't generate income.

This is a really complex situation that highlights how confusing tax software can be with edge cases. You're absolutely right that TurboTax should have caught this - when you entered "0" for both fair rental days and personal use days, that's mathematically impossible since the property exists somewhere for 365 days. Based on what others have explained here, it sounds like you need to go back and correct your filing. You should enter 365 days for personal use (since below-market rentals to friends/family are considered personal use), which would take you out of the Schedule E rental property track entirely. The good news is that if your maintenance fees are less than your property taxes, you likely don't need to report any income at all. But you should definitely get professional help or use one of the tools mentioned here to make sure you're handling the foreign aspects correctly - there are additional considerations for foreign properties that go beyond just the rental vs. personal determination. Don't feel bad about the confusion - this is one of those areas where the tax code is genuinely unclear and even tax professionals sometimes get it wrong!

Don't forget you can deduct mileage for all those deliveries! Standard rate was 67 cents per mile for 2024. Even with just $475 in income, the mileage deduction could potentially offset most of that.

Just to add another perspective - I was in almost the exact same situation last year with about $520 from DoorDash and Instacart combined. No 1099s from either company. I filed using FreeTaxUSA and it was pretty straightforward once I figured out the process. When you get to the self-employment section in TaxAct, look for something like "Other Income" or "Income not reported on tax forms" rather than trying to enter it as if you had a 1099. You'll basically create your own business income entry. I just put "Food Delivery Services" as the business description and entered my total earnings. The key thing is keeping good records of what you actually earned - screenshots from the apps, bank deposit records, whatever you have. And definitely track those miles like others mentioned. I drove about 900 miles total and that mileage deduction basically wiped out most of my self-employment tax liability.

Has anyone dealt with the reporting requirements for the PERSON WHO PAID the settlement? I'm on the other side of this - I had to pay a settlement last year and am confused about how to report the attorney fees portion on the 1099-MISC I'm issuing.

Just want to add some clarity based on my experience as a tax preparer - the key thing everyone's touching on is correct: if your settlement was SOLELY for physical injuries from your workplace accident, it's likely not taxable under IRC Section 104(a)(2). However, be careful about one thing: if any portion of that $42,500 was for lost wages or punitive damages (rather than just compensating for the physical injury and medical expenses), that portion WOULD be taxable. Check your settlement agreement carefully - sometimes these get lumped together. If it's truly all for physical injuries, you don't report it as income, and the 1099-MISC in Box 3 becomes irrelevant for your tax return. But keep all your settlement documentation because the IRS will have a record of that 1099-MISC being issued to you. Also, even if you determine it's non-taxable, some tax software will still prompt you to enter the 1099-MISC and then allow you to mark it as "not taxable due to physical injury settlement" or similar - this creates a paper trail showing you received and considered the form.

This is exactly the kind of detailed discussion I needed to see! I'm a newcomer to dealing with gambling taxes and had no idea about some of these complications. @Omar Zaki - your situation is very similar to mine. I had about $22K in slot winnings but probably $24K in total wagers throughout the year. Based on what everyone's saying here, I need to report the full $22K as income and then itemize the $22K in losses (not the full $24K since I can only deduct up to my winnings). The part about AGI impact is really eye-opening though. I'm on an income-driven student loan repayment plan, so even though my gambling was essentially break-even after losses, that $22K in winnings is going to bump up my monthly payments significantly. This is something I wish I had known before I started gambling regularly. Does anyone know if there's a way to minimize this AGI impact, or is it just an unavoidable consequence of gambling? It seems like the tax system penalizes gamblers even when they don't actually profit from their activities. Also, for record-keeping - I mostly used my player's card at two different casinos. Would getting annual statements from both casinos showing my total play and win/loss records be sufficient documentation for the IRS?

As someone who's been through multiple years of gambling tax reporting, I want to emphasize how important it is to start keeping detailed records RIGHT NOW if you haven't already. I learned this lesson the hard way after getting audited in 2022. The IRS Publication 529 specifically states that you need to maintain a gambling diary with: date and type of gambling activity, name and location of the gambling establishment, names of other people present, and amounts won or lost. This diary becomes crucial evidence if you're ever questioned. One thing I don't see mentioned much is the "professional gambler" designation. If you're gambling frequently enough and treating it like a business (which it sounds like some of you might be), you could potentially qualify to report gambling income and losses on Schedule C instead of as itemized deductions. This would avoid the AGI inflation issue everyone's talking about, but the IRS has very strict criteria for this classification. The professional gambler route requires proving that gambling is your primary source of income, you do it regularly and continuously, and you approach it in a businesslike manner with records and systems. It's a high bar to meet, but for serious players dealing with large volumes, it might be worth consulting a tax professional about. For most recreational gamblers though, the standard approach of reporting winnings as income and itemizing losses on Schedule A is the way to go - just be prepared for those AGI consequences!

This might be a dumb question but does anyone know a good tax software that handles options trading well? I've been using H&R Block but it seems totally confused by my covered calls and cash-secured puts.

I've been dealing with the same TD Ameritrade 1099-B confusion for years! One thing that really helped me was understanding that the "basis reported to IRS" distinction basically tells you how much work you have to do. When TD reports the basis, they're telling the IRS what you paid - so you just need to make sure your tax software captures the right gain/loss. When they don't report basis, you're on the hook to prove what you paid if the IRS ever asks questions. For your $63k trading volume, definitely pay attention to the wash sale adjustments. TD Ameritrade is pretty good about calculating these, but they only track wash sales within their own system. If you have accounts at other brokers or bought the same securities in a retirement account, you'll need to manually track those wash sales yourself. Also, since you mentioned futures trading - those Section 1256 contracts are actually treated more favorably tax-wise because of that 60/40 long-term/short-term split, regardless of holding period. So even if you held a futures contract for just one day, 60% of the gain gets long-term capital gains treatment. Pretty nice tax advantage compared to regular stock trading!