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.

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.

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 successfully used the IRS's "Get Transcript" online to get copies of previously filed 8606 forms? I need to see what I submitted for the last few years to fix my backdoor Roth basis calculations.

For anyone else filing corrected 8606 forms for their backdoor Roth IRA: I just went through this process and prepared a simple cover letter to attach to my corrected forms that read: "Please find enclosed corrected Forms 8606 for tax years 2020, 2021, and 2022. These corrected forms properly reflect the basis of non-deductible IRA contributions and Roth conversions that were made in each year. The original forms contained calculation errors but the corrections do not change my tax liability for any year." The IRS processed them without issue and I received confirmation letters about 8 weeks later.

Just FYI - the IRS has a specific form for self-employment income called Schedule C. All your handyman and DJ money goes there. You'll pay regular income tax PLUS self-employment tax (about 15.3%) on that income. But the good news is you can deduct expenses like: - Tools and equipment - Mileage driving to jobs (58.5 cents per mile) - Portion of phone bill used for business - Advertising costs - Software or subscriptions related to your work - Office supplies For your roommate situation, that's different - look up "Schedule E" for rental income. Keep good records of EVERYTHING. I use a simple spreadsheet and take pictures of receipts with my phone. Start organizing now before tax season and you'll thank yourself later!

I was in your EXACT situation last year with my woodworking side hustle! The thing that saved me was keeping everything super organized. I created a separate checking account JUST for side business stuff - it helps so much come tax time! Also, get a simple expense tracking app to record everything. For cash, I immediately write it down in my phone notes with the date and amount. Then once a week I move that info to a spreadsheet. The IRS doesn't mess around with unreported income. My sister tried to hide her Etsy income and got hit with a massive audit and penalties. Not worth the stress!!