Has anyone in this situation tried to coordinate with their parents to bunch medical expenses into one tax year? My mom and I are trying to plan some expensive procedures and figuring out if we should schedule everything in December or January.

This is a tricky situation that I've seen come up a lot. Since your parents paid the medical expenses directly, they're the ones who can claim the deduction - not you. The IRS is very clear that medical expenses can only be deducted by the person who actually made the payment, regardless of whose name is on the bill. However, there might be a silver lining here. If your parents provided more than half of your support for the year (which sounds possible given your work situation and the fact they paid $14,000 in medical bills), you could be considered their "qualifying relative" for medical expense purposes. This would allow them to include the medical expenses they paid for you when calculating their medical deduction. For future expenses, consider having your parents gift you the money first, then you pay the medical providers directly. This way you'd be able to claim the deduction on your return. Just make sure to document everything properly and keep records of who actually made each payment. Given your low income this year, it's definitely worth having your parents check if they can benefit from the medical expense deduction, especially if they have other medical costs that might push them over the 7.5% AGI threshold.

I don't think anyone's addressed your marriage plans for 2024. Remember that your filing status is determined by your status on December 31st of the tax year. So if you get married anytime in 2024, you'll be considered married for the entire 2024 tax year. If you're married filing jointly in 2024, you can't file as Head of Household, regardless of your parent situation. If you're married filing separately, you might qualify for HOH in very limited circumstances (like if you're considered "unmarried" because you lived apart from your spouse for the last 6 months of the year). For 2023 though, since you're still single, the dependent parent question is definitely worth figuring out!

Just wanted to add another perspective on this since I dealt with something very similar. My parents are also married and on Social Security only, and I was able to claim my mom as a dependent last year. The key thing that made it work was documenting exactly how much support I provided versus their total support needs. I kept detailed records of everything - mortgage payments I made for them, utilities, groceries, medical expenses, home repairs, etc. Then I calculated their total living expenses for the year and proved I paid more than 50%. For the gross income test, since Social Security was their only income and it wasn't taxable at their income level, my mom passed that test easily. The joint return test was satisfied because they didn't file any return at all. However, I couldn't qualify for Head of Household because they live in their own home, not with me. A parent can be a qualifying person for HOH even if they don't live with you, but only if you can claim them as a dependent AND you pay more than half the cost of maintaining their household as their main home. One thing to watch out for - make sure you have really solid documentation of all the support you're providing. The IRS can be pretty strict about this if they audit dependency claims.

Don't forget that if your father's estate is large enough, you might also need to file an estate tax return (Form 706) within 9 months of death, even if no estate tax is due. For 2025, this applies to estates worth over $13.61 million. Different from the income tax issues everyone's discussing.

Just wanted to add my experience as someone who went through this recently with my grandmother's estate. The step-up in basis rule really is a lifesaver - we sold about $180,000 in stocks to pay off her medical debts and ended up with only about $3,200 in capital gains because we acted quickly after her passing. One practical tip: keep very detailed records of everything. I created a spreadsheet tracking each asset's date-of-death value, sale date, sale price, and resulting gain/loss. This made filing the Form 1041 much easier and gave me confidence that everything was calculated correctly. Also, if you're working with multiple brokerage firms, some are much more helpful than others in providing the date-of-death valuations. Vanguard was fantastic - they provided a detailed statement within 48 hours. Schwab took nearly three weeks and required multiple follow-ups. Just something to keep in mind as you plan your timeline for settling the debts.

Has anyone actually tried claiming this on their taxes? I'm curious if the IRS has explicitly denied these claims or if it's just that tax professionals don't think it would work.

Thanks for sharing this specific case example! That's exactly the kind of real-world precedent we need to hear about. It sounds like the IRS is being pretty clear that they're going to look at the fundamental design and purpose of the item rather than how someone chooses to use it. @Manny Lark - this might save you from going down the same path and having to deal with additional paperwork and potential penalties. Even though your usage pattern makes logical sense, it seems like the IRS has already made their position clear on this specific scenario. I'd definitely recommend looking into those dedicated home battery systems that @Demi Hall mentioned. With your 135kWh truck, you clearly understand the value of large battery capacity - a proper home system would give you the tax benefits without any regulatory risk.

Sometimes when they do manual adjustments it defaults to check even if u picked DD. But ive seen it go both ways tbh

From my experience, when they remove a freeze code manually like that, it usually goes back to your original payment method (direct deposit in your case). The agent probably said check because that's their default response, but I've seen most people still get DD when they originally selected it. Check your transcript for the 846 code in the next day or two - that'll tell you for sure how it's coming!