Anyone using tax software to handle this? I tried using TurboTax but it's still confusing me with how it imports the 1099-B and then what goes where.

As someone who's dealt with Schedule D and Form 8949 for several years now, I'd recommend double-checking your broker statements against what you report. Sometimes brokerages make errors on the acquisition dates or cost basis, especially if you transferred stocks between accounts. For your 6-month holding period stocks with $3,200 in profits, you're definitely dealing with short-term capital gains (taxed as ordinary income). Make sure each transaction on Form 8949 Part I matches exactly what's on your 1099-B forms - the IRS computer system will flag any discrepancies. One tip: if you have a lot of transactions, consider grouping identical securities with the same acquisition and sale dates on a single line of Form 8949, rather than listing each share lot separately. This keeps the form cleaner while still being compliant. Also, don't forget that short-term gains are added to your regular income for tax purposes, so depending on your tax bracket, you might owe more than you expect. Worth setting some money aside if you haven't already!

2 Has anyone used TIN matching with partnerships? We have an unusual situation where our LLC (taxed as partnership) needs to issue 1099s to several vendors, but we've heard that partnerships have different requirements for accessing the service.

I went through this exact process earlier this year for our consulting firm and wanted to share a few additional tips that might help: 1. Make sure you have your business banking information handy when applying - the IRS will ask for account details to verify your business identity during the e-services registration. 2. If you're planning to use the bulk upload feature (highly recommend for more than a few vendors), practice with the file format first. The IRS is very picky about the CSV layout and will reject your entire batch if even one row is formatted incorrectly. 3. Keep in mind that TIN Matching results are only valid for the calendar year you receive them. So if you verify TINs in December 2024, you'll need to re-verify them again for 2025 filings. 4. Pro tip: Run your TIN matching in early November if possible. This gives you time to reach out to vendors with mismatched information and get corrected W-9s before the 1099 filing deadline. The whole process definitely has a learning curve, but once you're set up it saves SO much time compared to dealing with IRS notices for incorrect TINs after the fact.

does anyone know if doing doordash delivery for like 3 months would count the same way? i made maybe 6k total but didnt have any taxes taken out cuz its 1099 work. should i still file?

Just wanted to add that you should also keep an eye out for your W-2 form, which should arrive by January 31st. This will have all the exact numbers you need - your total wages in Box 1 and federal income tax withheld in Box 2. Even though you only worked 6 months, employers are required to send W-2s to anyone who earned income during the tax year. Once you have that form, you'll know exactly how much was withheld and can determine your potential refund amount. Most free tax software can handle your straightforward situation, and with your income level, you should qualify for free filing through the IRS Free File program. Don't let the partial year of work discourage you from filing - it's actually pretty common and the process is the same as filing with a full year of income!

Don't forget that for gambling, you have to itemize deductions on Schedule A to claim losses. This means giving up the standard deduction which is $14,600 for single filers in 2025. If your total itemized deductions (including gambling losses, mortgage interest, charitable contributions, etc.) don't exceed your standard deduction, it might not make sense to deduct gambling losses at all.

For your 2024 situation where you didn't report small winnings under $600, you're probably fine since the amounts were minimal and you didn't receive any tax forms. The IRS typically focuses on larger unreported income. For this year with the $20,000 PayPal 1099-K, that's reporting gross payment volume, not taxable income. You'll need to separate your actual gambling winnings from deposits/withdrawals. Since you're only up $135 on FanDuel and didn't get a 1099 from Prizepicks, your actual taxable gambling income is likely very small. The key is keeping good records going forward. Download transaction histories from both platforms showing all bets placed and winnings received. Your tax professional should be able to help you properly report the actual winnings as income while ensuring you don't overpay based on the inflated 1099-K amount. Most importantly, don't panic - this is a common situation with payment processors issuing 1099-Ks for gross transactions rather than net gambling profits.

Question for anyone who's done this - does grouping require amending previous returns? I'm in a similar situation with a property LLC and operating business, and filed separately for the last two years.

This is exactly the kind of situation where activity grouping can be a game-changer! Since you have common ownership of both LLCs and clear operational interdependence (PropCo exists primarily to serve OpCo), you should have a strong case for grouping. The key thing to remember is that once you group these activities and you materially participate in the restaurant business, the entire grouped activity becomes non-passive. This means those $78,000 in historic rehabilitation credits would no longer be trapped as passive credits - you could use them against your restaurant income or even your wife's non-passive income. Make sure to document the business reasons for grouping (shared management, operational interdependence, common ownership) in your election statement. Given the substantial credits at stake, it might also be worth getting a second opinion from a tax professional who specializes in passive activity rules before making the election, just to ensure you're maximizing the benefit and meeting all requirements.