Just be careful with those gambling winnings. I had a similar situation with $900 from DraftKings. Even though you need to file, you might not actually get that refund FreeTaxUSA is showing.

Great point about the gambling winnings tax withholding! Since you mentioned FanDuel, they should have sent you a 1099-MISC if your winnings were over $600 (which yours were at $750). Check if they withheld any federal taxes from your winnings - if not, you might actually owe money instead of getting that refund FreeTaxUSA showed you. Also, since you're filing as someone who can be claimed as a dependent, your standard deduction will be limited to the greater of $1,150 or your earned income plus $400 (up to the standard deduction amount). This could significantly affect whether you actually get a refund or owe taxes on those gambling winnings. I'd double-check those numbers in FreeTaxUSA to make sure it's accounting for your dependent status correctly!

Don't overlook state taxes! Federal is only part of it. Some states don't offer any primary residence exclusion even when federal does. I learned this expensive lesson in California last year.

The conversation about moving back into your rental property is spot on, but I'd also suggest running the numbers on the timing carefully. You mentioned the tenant's lease expires in November - that could be perfect timing to move in and establish it as your primary residence for the required 2 years before selling. One thing to consider: if you're planning to eventually sell both properties to buy a house, you might want to stagger the sales across different tax years to avoid pushing yourself into higher tax brackets or triggering the 3.8% NIIT that Ava mentioned. Selling both in the same year could create a significant tax burden even with the primary residence exclusions. Also, keep detailed records of when you move in/out of each property. The IRS can be pretty strict about proving the 2-out-of-5-years requirement, especially if you're switching between properties. Utility bills, voter registration, and other documentation showing your actual residence will be important if you're ever audited.

Has anyone used FreeTaxUSA for reporting Twitch income? TurboTax keeps trying to charge me for the self-employment version even though I just need to file a Schedule E for royalties.

This is exactly the kind of confusion I had when I first started getting 1099s from my side income! The distinction between royalties and self-employment income is really important and can save you money. Just to add to what others have said - since you're operating at a net loss, make sure you keep detailed records of all your streaming-related expenses (equipment, software subscriptions, games, internet upgrades, etc.). Even though you're reporting on Schedule E for the royalty income, you can still deduct ordinary and necessary expenses against that income. Also, don't let TurboTax upsell you into the self-employment package if you don't need it! The basic version should handle Schedule E just fine. If your tax software is pushing you toward Schedule C, it's probably because it's seeing "1099" and assuming it's all self-employment income, but as others have explained, the 1099-MISC Box 2 royalties are different. One last tip - keep good documentation about the hobby vs. business question. The IRS looks at factors like whether you're trying to make a profit, how much time you spend on it, and whether you have the expertise to make it profitable. Since you mentioned you're still in the "costs money" phase, documenting your efforts to grow the channel and become profitable could be helpful if this ever comes up.

I'm a bit confused. What exactly is Box 14 used for on a W-2? Is that even taxable income?

I actually work in payroll and see this situation fairly often! When box 14 has a tiny amount but box 1 is blank, it's usually something like a final expense reimbursement, a small bonus adjustment, or even a rounding error from benefits calculations that got processed after your last regular paycheck. The key thing is to look at what's written next to that 6 cents in box 14 - there should be a description or code. If it just says "Other" with no explanation, you can definitely enter $0 in box 1 for TurboTax. Sometimes you need to go into the advanced W-2 entry mode rather than the simplified version. If TurboTax keeps rejecting it, try FreeTaxUSA or Credit Karma Tax - they tend to be more flexible with unusual W-2 situations. You shouldn't have to paper file for something this minor!

Wait im confused. I've been selling on Etsy for years and never worried about this. I just report whatever is on my 1099k. Are you guys saying im doing it wrong??? Now im stressing that I've been doing my taxes incorrectly this whole time!

As someone who's been dealing with this exact issue across multiple platforms (eBay, Etsy, Amazon), I can confirm this timing difference is incredibly frustrating. What helped me was creating a simple reconciliation spreadsheet that tracks three columns: 1) Sale date, 2) Payment received date, and 3) Platform payout date. This way I can easily see which sales fall into different tax years based on when funds were actually available. I decided to stick with cash basis accounting to match my 1099-Ks, even though it means some December sales don't show up as income until the following year when the platforms release the funds. The key thing I learned is that consistency matters more than which method you choose. Pick either cash or accrual and stick with it year after year. I keep detailed notes in my records explaining any timing differences, which gives me peace of mind if I ever need to explain the numbers to the IRS. For what it's worth, my CPA told me that most small online sellers use cash basis specifically because it eliminates this headache. The platforms are essentially acting as your payment processor, so treating income as received when they release it makes perfect sense from an accounting standpoint.