That's really good advice! Would you recommend asking them any specific questions to gauge their knowledge about medical deductions? I wouldn't even know how to tell if they're giving me good answers since I don't know much about this stuff myself.

Ask them specifically about the 7.5% AGI threshold for medical expenses and how they would help determine if you should itemize. A knowledgeable preparer will explain that medical expenses are only deductible for the amount exceeding 7.5% of your adjusted gross income, and they'll want to know if you have other potential deductions that could make itemizing worthwhile. You could also ask what types of medical expenses are deductible that people commonly miss. They should mention things like mileage to medical appointments, lodging while receiving medical care away from home, home modifications for medical purposes, or certain insurance premiums. If they only mention obvious things like doctor bills, they might not have specialized knowledge.

Thats true, my local HR Block has an enrolled agent who specializes in medical deductions. Shes way better than the seasonal people they hire and not much more expensive. I've used her for 3 years now.

You absolutely cannot ignore it! The IRS receives a copy of every 1099-K, and their systems automatically match them to your tax ID. If you don't account for it somehow on your return, you'll likely get a CP2000 notice (automated underreporting notice) which is basically the IRS saying "hey, we think you didn't report all your income." The correct approach is to report it and then exclude it with an explanation. Most tax software (including CashApp Taxes) has a way to indicate the money isn't taxable income. This satisfies the reporting requirement while ensuring you don't pay taxes on money that isn't actually income.

Thanks for explaining! That makes sense about the IRS matching the forms. So better to report it with the explanation than to trigger an automatic flag in their system. I'll make sure to include it in CashApp Taxes and check that box saying it's not taxable income.

I managed to get Square to issue a corrected 1099-K last year, but it took persistence. The key was escalating beyond the first-level support. I had to specifically request to speak with their tax reporting department. It took about 6 weeks, but they eventually issued a corrected form. In the meantime, I filed my taxes as others here suggested - reporting the 1099-K but indicating the amounts weren't taxable. That way if the correction never came, my taxes were still accurate.

Isn't setting up a 501(c) really expensive and complicated though? I heard you need lawyers and stuff.

It's not as bad as people think. For a small organization, filing for 501(c)(3) status using Form 1023-EZ is relatively straightforward if your annual gross receipts are under $50,000. The filing fee is around $275. You don't necessarily need lawyers, though having someone with experience look over your application can help. There are also online services that guide you through the process for a few hundred dollars. The main requirements are having proper bylaws, a board structure, and clear charitable purpose. Once established, annual maintenance is just filing a simple Form 990-N if you stay under the $50,000 threshold.

This is actually what we do for our school's charity auction. People make checks directly to the charity, and we just collect them. Simplifies everything tax-wise.

That's really interesting! I hadn't heard of a landlord contribution agreement before. Did your brother's arrangement require monthly payments to still be made, or was it entirely offset by the improvements? My situation is more informal - I help with utilities and maintenance but don't pay a set "rent" amount.

The arrangement didn't require full elimination of rent payments. They structured it so a portion of what would have been market-rate rent was offset by the documented improvement costs. There was still some payment happening to establish a legitimate landlord-tenant relationship, but significantly reduced. The key was having everything in writing with fair market values established for both the rent and the improvements. They also took photos before/after and kept all receipts. Their tax professional basically said the most important thing is showing this is a legitimate business arrangement, not just a family helping each other out informally. The more formal documentation you have, the better position you're in if questions come up.

Doesn't the IRS also have some kind of recapture rule if you claim these credits and then move out or sell within a certain time period? I feel like I read something about that when I was considering solar panels.

If I find different refund amounts between software, how do I know which one is correct? Should I just go with the one that gives me the bigger refund?

You should never simply choose the software that gives you the bigger refund without understanding why there's a difference. A larger refund might be incorrect and could potentially trigger an audit. If you find different results, dig into the actual tax forms and compare them line by line to see where the differences occur. The most common discrepancies happen with education credits, business expense categorizations, or retirement contribution deductions. When you find the specific lines that differ, research that particular tax topic or consult with a professional about that specific issue.

Does this work with state taxes too or just federal?