I'm confused about something... do you need to claim the person as a dependent for THE ENTIRE tax year to deduct their medical expenses? My brother moved in with me in September and I paid for his LASIK in November. He'll qualify as my dependent for next year but not for the full current year. Any advice?

Just want to add some clarity on the dependency rules since there seems to be some confusion in the thread. For medical expenses, you can deduct costs paid for yourself, your spouse, and your dependents. The key dependency tests for adult relatives like siblings are: 1. **Gross Income Test**: Their gross income must be less than $4,400 for 2023 (this changes annually) 2. **Support Test**: You must provide more than 50% of their total support for the year 3. **Relationship Test**: They must be a qualifying relative (siblings qualify) 4. **Joint Return Test**: They can't file a joint return with a spouse (unless only to claim a refund) Emily, since your sister had the procedure done and you have receipts in your name, you're on the right track documentation-wise. The real question is whether she meets the dependency criteria above. If she works and earns more than $4,400, unfortunately you can't claim her medical expenses even though you paid for them. One more thing - don't forget that medical expenses are only deductible to the extent they exceed 7.5% of your AGI, and you must itemize to claim them. With the current high standard deduction ($13,850 single/$27,700 married filing jointly for 2023), many people find itemizing doesn't provide additional tax benefit.

Has anyone used TurboTax for reporting something like this? I'm in a similar situation (smaller amount though) and wondering if the software walks you through it properly or if I need to consult a tax professional.

I'm dealing with something very similar right now - helped fund a friend's rental property purchase with a 20% profit share agreement when they sell. After reading through all these responses, I'm leaning toward the "Other Income" approach on Schedule 1 since it was a one-time informal arrangement. One thing I'm curious about though - did anyone here keep specific documentation of their arrangement? I only have text messages between me and my friend discussing the terms. Is that sufficient, or should I create something more formal after the fact to document the agreement? I want to make sure I have proper backup if the IRS ever questions how I reported it. Also, for those who went the Schedule 1 route, did you include any additional explanation beyond the brief description line, or is "Investment return from private loan" or similar enough detail?

To offer a different perspective, I went from TurboTax to a CPA back to a hybrid approach. The CPA I found charged $1,800 annually (no crazy initiation fee) and honestly didn't provide much more value than TurboTax for my situation (2 rentals, W2 income, and some RSUs). What I do now: 1. Use TurboTax to prepare most of my return 2. Pay a CPA $350 for a 2-hour consultation to review it and suggest optimizations 3. Implement their suggestions myself in TurboTax I get 90% of the benefit at 25% of the cost. The one-time review catches things I miss while letting me maintain control of my filing. And I have documentation from a professional if questions ever come up. Whatever you decide, that $6500 "initiation fee" is absolutely outrageous and you should run far away from that particular CPA.

I switched from TurboTax to a CPA two years ago and it's been worth every penny, but that $6500 onboarding fee is absolutely ridiculous! I have a similar situation - multiple rental properties, RSUs from my tech job, ESPP participation, and various investment accounts. My CPA charges $1,800 annually with no initiation fee whatsoever. The biggest value I've gotten is proactive tax planning throughout the year. My CPA calls me before major RSU vesting dates to discuss tax withholding strategies, helps me time rental property improvements for maximum deduction benefit, and even suggested converting one of my properties to a short-term rental which qualified for different depreciation rules. Last year alone, she identified about $5,200 in additional deductions that TurboTax completely missed - mostly around rental property expense categorization and proper RSU cost basis reporting. TurboTax's "experts" kept giving me conflicting advice about whether certain rental expenses were repairs vs improvements. My advice: definitely make the switch to a CPA, but interview at least 3-4 who specialize in tech employees with real estate. Ask specific questions about RSU taxation strategies and rental property optimization. Anyone charging a massive upfront fee is probably not the right fit. Good CPAs earn their money through quality ongoing service, not gatekeeping fees.

Question - how does this work with AGI limitations? I know there are percentage limits on charitable deductions but they seem to vary based on the type of property and organization. Would donating art to a museum be different than donating it to something like a hospital charity auction?

One thing I haven't seen mentioned yet is the Form 8283 requirements and how they interact with the $5,000 threshold. If your total noncash charitable deductions for the year exceed $500, you need to file Form 8283. But the really important part is Section B - if any single item or group of similar items is valued over $5,000, you need a qualified appraisal AND the appraiser must sign Section B of the form. What caught me off guard when I donated some artwork last year is that the IRS can also request additional documentation even years later. They have the right to contact your appraiser directly to verify the appraisal, and if the appraiser can't substantiate their valuation methods or doesn't meet the IRS qualification requirements, your entire deduction could be disallowed. Also worth noting - if you're donating multiple pieces, the IRS looks at the total value of "similar items" together. So if you donate three paintings worth $4,000 each in the same tax year, that's treated as $12,000 of similar property and triggers all the higher-value requirements even though each individual piece is under $5,000.

11 Did the IRS send you a specific notice number? Like CP-2000 or something similar? That would help identify exactly what triggered this in their system. The form numbers matter a lot for resolving these issues. Also, SAVE EVERYTHING. Every letter, every notice, and document every phone call (date, time, representative name/ID, what was discussed). The deceased taxpayer issue often bounces between departments, and having a paper trail is crucial if you need to escalate.

This is such a frustrating situation, but you're definitely not alone! I went through something similar two years ago when the IRS decided I was deceased right in the middle of tax season. Here's what I learned from my experience: The "deceased" flag usually comes from the Social Security Administration's Death Master File, often due to clerical errors or mix-ups with similar names/SSNs. The key is to tackle this systematically: 1) **Start with SSA immediately** - Don't wait. Visit your local SSA office with multiple forms of ID (driver's license, passport, birth certificate, etc.). Request they correct their records and give you written confirmation. 2) **Get everything in writing** - When SSA fixes their records, ask for an official letter stating the error was corrected. You'll need this for every other agency. 3) **File a paper return** - Unfortunately, e-filing likely won't work until this is resolved. Include a cover letter explaining the situation and attach a copy of the SSA correction letter. 4) **Check your credit reports** - The deceased flag can spread to credit bureaus, so monitor all three and dispute any incorrect death records immediately. The whole process took me about 2-3 months to fully resolve, and my refund was delayed, but I did eventually get everything sorted out. Hang in there - you'll get through this bureaucratic nightmare!