Another option - I use duplicate receipt books with "Buyer" and "Seller" clearly labeled at the top. That way I just fill in the info and circle which one I am in the transaction. Makes it super clear for tax time which role I was playing, especially when I'm buying from individuals.

Don't overthink it honestly. I've been flipping computer parts for years and I just keep a google doc where I record all my purchases and sales. As long as you have some record of what you bought, when, and for how much, you're covered for basic tax purposes. Receipt books are great but not absolutely necessary.

Another option besides what others mentioned: check if your employer reported your wages electronically to the Social Security Administration. You can create an account on ssa.gov and view your detailed earnings record. This won't have your withholding info, but it will show what wages were reported under your SSN. Also, if you have your final paystub of the year (the last one from December), it should have your year-to-date totals which will give you everything except for what you earned in January. For the unpaid wages, definitely file a complaint with your state labor board. In most states, you can get penalties added on top of your unpaid wages if they don't pay you within a certain timeframe after termination.

I used to work in payroll, and just wanted to add - definitely check your last paystub from December because it should have your year-to-date totals for everything (earnings, federal withholding, state withholding, etc). That covers everything except your January earnings. For January, if you got paid via direct deposit, your bank statement will show exactly what you received. Then you just need to figure out the withholding for those January payments. Most payroll systems use the same withholding percentages unless you changed your W-4. So if your federal withholding was consistently 15% of your gross pay, you can apply that same percentage to your January earnings to estimate January's withholding.

Another thing to consider is that if you pay your taxes with a credit card (through H&R Block or any tax software), there's always a processing fee of around 2-3%. So even if you could get cash back on the tax payment (which you can't), you'd still be paying that processing fee which would likely cancel out much of the benefit. I usually just set up direct payment from my bank account through the tax software to avoid those fees completely.

Has anyone confirmed if the 16% is actually showing up in their Rakuten account after filing? Sometimes these offers have exclusions in the fine print. I saw it advertised but wanted to check if people are actually getting the full amount before I commit to H&R Block.

11 Another tip - before going to your appointment, organize the Robinhood document a bit. I paperclip the summary 1099 page at the front, then group the detailed transaction pages together by category (stocks, dividends, crypto, etc.). My tax person really appreciated this small effort since it made finding specific information easier. Still bring all the pages though!

5 Question - does anyone know if we should be bringing previous years' Robinhood documents as well? I still have last year's 20-page monster file and wasn't sure if the tax preparer would need that for comparison or to check for carryover losses.

Has anyone considered the potential partial interest rules here? If the property has a mortgage or if the OP is only donating a portion of the property rights, that complicates things significantly. The charitable deduction could be limited in ways beyond just the AGI limitations others have mentioned.

Don't forget about state tax implications too! Depending on your state, the rules for charitable deductions of property might differ from federal rules. Some states limit itemized deductions or have different AGI percentage limitations. In my state (CA), they have additional documentation requirements beyond what the IRS asks for.