That's actually really good advice I hadn't thought about. The site does have a transaction history but I'm not sure how long they keep it. Do you think I should also be documenting the gift card purchases separately? And should I be using the transaction hash from the blockchain as well?

Yes, document the gift card purchases too! Screenshot receipts, confirmation emails, anything showing you bought them. This creates a clear paper trail of the full transaction flow: money → gift cards → gambling site → crypto winnings. The transaction hash from the blockchain is absolutely essential documentation. That's your definitive proof of exactly when you received the ETH and how much. Save that information along with a record of what ETH was trading for at that exact moment. Services like CoinMarketCap let you look up historical prices at specific times. This combination of evidence makes your cost basis virtually indisputable if questions ever come up.

I used FreeTaxUSA last year for something similar. You need to report the gambling winnings separately from the crypto. Under "Income" there's an "Other Income" section where you report gambling winnings. Then under "Investments" you add the crypto with your cost basis being the value when you received it. It's not super intuitive but works fine once you set it up right.

Thanks, that helps a lot! I was trying to do everything under the crypto section which explains why I was getting confused. I'll separate the gambling income like you suggested.

Thanks for the accounting perspective! Would it be worth asking them directly if they plan to issue a 1099 for this reimbursement? Or is there specific language I should use when I submit the W9 to make it clear this shouldn't be treated as income?

Yes, it would definitely be worth asking them directly if they plan to issue a 1099 for the reimbursement. A simple email saying "I'm submitting the W-9 as requested, but want to confirm you won't be issuing a 1099 for this payment since it's a reimbursement for expenses I incurred due to construction issues, not income" should do the trick. As for specific language when submitting the W-9, I'd attach a brief cover letter stating: "This W-9 is being provided solely for your vendor setup requirements. The $750 payment represents reimbursement for mold testing expenses I incurred as a result of construction defects, not payment for services or taxable income. Please ensure this is properly coded in your accounting system as an expense reimbursement to prevent incorrect 1099 reporting." That clearly documents your position if there are any questions later.

Bad advice. If a company asks for a W-9, refusing to provide it could cause them to withhold payment entirely or potentially subject you to backup withholding at 24%. Much better to provide the W-9 with a clear explanation that this is a reimbursement, not taxable income.

I used FreeTaxUSA Pro last season and it was decent for basic returns. The interface isn't as polished as the big names but it gets the job done. State returns are extra though, like $15 each.

Good point! I wasn't planning to charge anything since I'm just getting experience, but I'll look into getting a PTIN anyway to do things properly.

Your gig work from Uber and DoorDash shouldn't go on Line 1h. That income is considered self-employment income and should continue to be reported on Schedule C. The "Other earned income" on Line 1h is generally for earnings that are treated as wages but don't fit in the other categories. As a self-employed gig worker, you'll still report your income and expenses on Schedule C, calculate your net profit or loss, and then that flows to Schedule 1 and ultimately to Form 1040. These changes to Line 1 don't change the fundamental way gig workers report their income.

Tax software companies update their programs every year based on IRS changes. TurboTax, H&R Block, and other major tax software should have all the new form changes implemented before filing season begins. They usually start updating their systems as soon as the IRS finalizes the forms.

Thank you for the detailed explanation! I called Chase this morning and they said there's no specific hold, but they do have a standard processing time for ACH transfers. The customer service rep told me the money should be available tomorrow, which is 3 days before the settlement date. That matches what you're saying about them making funds available before actual settlement.

Glad to hear it's working out! That's typical for Chase. They usually release tax refund funds within 1-2 business days of receiving the ACH notification, regardless of the settlement date. The settlement date is more about the backend banking processes than when you can access your money. If you want to avoid this next year, some tax preparation services offer options to receive your refund on a prepaid card which sometimes posts a bit faster than traditional bank ACH transfers. Though personally, I think waiting an extra day or two for the money to hit your regular account is worth avoiding the fees those cards sometimes charge.

This is great advice! I work at a credit union and we do make government deposits available immediately, but many people don't realize that policies vary drastically between financial institutions. Another tip: if you file very early in tax season, refunds can sometimes take longer to process even after showing as "pending" because the IRS and banks are dealing with high volumes.