Building on this - make sure you're tracking those suspended losses separately from your basis tracking. I messed this up one year and it was a nightmare to fix. The amount that reduces your basis is ONLY what you actually deducted on your tax returns, not what was calculated but suspended.

Yes, bonus depreciation is phasing down. It's 80% for property placed in service in 2023, and will drop to 60% for 2024, then 40% for 2025, 20% for 2026, and then zero after that (unless Congress extends it again). So if you're planning major purchases, there's definitely a tax advantage to doing it sooner rather than later.

Thanks for bringing this up - I hadn't considered the statute of limitations angle. Do you think filing the Form 8606 now for those old contributions might trigger some kind of review of those past tax years?

Filing Form 8606 now for old contributions typically doesn't automatically trigger an audit, but it does put those years on the IRS's radar. The good news is that you're trying to comply with the rules by properly documenting your basis in the IRA, which looks better than if they discovered the unreported contributions some other way. The key is documentation - make sure you have records of all those contributions and be prepared to show they were made with after-tax dollars. If you're concerned, working with a tax professional who specializes in IRA issues might be worth the investment to ensure everything is handled properly and to help respond if the IRS does have questions.

This is incorrect information. The Tax Cuts and Jobs Act eliminated the deduction for IRA losses completely through 2025. Even before that, claiming such losses was extremely difficult and rarely beneficial due to the AGI limitations. Please don't give tax advice if you're not certain - it could cause serious problems for the OP.

Yes! I just double-checked and found it in the supplemental pages! There's a whole separate section for "Proceeds from Broker and Barter Exchange Transactions" that has all the info I need, including acquisition date and cost basis. Thanks for pointing this out - I was only looking at the first page.

Glad you found it! Robinhood's tax documents can be confusing because they combine different forms into one package. That supplemental section is actually the most important part for crypto transactions since it contains all the details you need for Form 8949. Just make sure you're using the correct acquisition dates since that determines whether it's long-term or short-term capital gains.

Yep, happened to me too. The cost basis on my 1099-B was off by about $25 compared to what my actual purchase price was. I had to file a Form 8949 with code B to indicate the cost basis was reported incorrectly to the IRS.

Thanks for the reminder about the Section 199A deduction! Is that handled automatically through Form 8995A or do I need to do something else to claim it? For the HSA, I'm contributing the maximum for individual coverage. One question though - if I switch to family coverage mid-year, can I contribute the full family amount or is it prorated?

Form 8995A is specifically for calculating your Section 199A (Qualified Business Income) deduction, so no need to do anything additional. It flows automatically to your 1040. For HSA contributions after switching to family coverage mid-year, it gets a bit complicated. You can actually contribute the full family maximum ($8,300 for 2024) if you're still covered by a family HDHP on December 1st and remain covered for the full calendar year of 2025 (called the "last-month rule"). If you don't maintain coverage through December 2025, you'd need to prorate your contribution based on how many months you had each type of coverage.

Just a quick correction - the SE tax is actually 15.3% (12.4% Social Security + 2.9% Medicare) on that 92.35% of net earnings, up to the Social Security wage base limit ($168,600 for 2024). Then 2.9% Medicare tax continues beyond that with no limit, plus an additional 0.9% for high earners. But your point about deducting half on Schedule 1 is super important - loads of people miss that and it's a significant deduction!

This is really helpful - I hadn't thought about the pass-through issue. In my case, the artists are receiving payment directly from their platforms and then sending me my percentage (usually 15-20%). So if they make $1000, they'd send me $150-$200 via Venmo. Does that simplify things since I'm only receiving my commission portion?

That definitely simplifies your situation! Since you're only receiving your commission portion directly, there's no pass-through income to worry about. The full amount you receive through Venmo is indeed your business income that should be reported on your Schedule C. Just make sure you're tracking each payment received with details on which artist it came from, what platform earnings it relates to, and the commission percentage applied. This documentation will help support your reported income if you're ever questioned. It's also smart business practice to send your artists an annual statement showing the total commissions they paid you, both for their records and yours.

This might be overkill for small payments though. I pay VAs in the Philippines less than $5k each per year and my accountant said as long as I have good documentation of the work performed and payments made, I don't need to worry about additional foreign reporting forms. Might depend on the dollar amount?