I'm a nurse and see this issue come up with patients all the time. The rule I always tell them is: if you prepaid for a SPECIFIC procedure with a set date and service, it's deductible when paid. If you put money into a general account or prepaid without knowing exactly what services you'd get, you have to wait until you actually get the service. Also make sure the medical expense is actually deductible. Remember you can only deduct the amount that exceeds 7.5% of your AGI, and only if you itemize deductions instead of taking the standard deduction.

One thing nobody's mentioned - make sure you keep REALLY good documentation. I went through an audit for medical expenses and they wanted to see proof of when I paid AND when I received services. Save everything - receipts, appointment confirmations, insurance EOBs, etc. The IRS is being super picky about medical deductions lately.

Just a heads up that these volunteer expense deductions only help if you itemize! With the standard deduction being $25,900 for married filing jointly in 2022, it might not be worth itemizing unless you have lots of other deductions like mortgage interest. I found that out the hard way after tracking all my scout leader expenses!

Great question! As others have mentioned, you unfortunately can't deduct the value of your time or professional services, but you can definitely deduct out-of-pocket expenses. One thing I haven't seen mentioned yet is that you should also track your mileage for any trips specifically related to your volunteer photography work - like going to the school just to pick up equipment, scouting locations for photo shoots, or making special trips to deliver finished photos. That adds up faster than you'd think at 14 cents per mile! Also, if you're using your home computer/internet for editing and uploading photos for the school, you might be able to deduct a portion of those costs too, though you'd need to calculate what percentage of usage is specifically for volunteer work vs personal use. The key is really good record-keeping - date, purpose, amount for every expense. Even small things like USB drives to transfer photos or cloud storage subscriptions if you're using them to share images with the school can add up to meaningful deductions if you itemize.

Just to throw another option out there - have you considered a qualified opportunity zone investment? If you're facing a big capital gains hit, you could potentially defer those gains by investing in a QOZ within 180 days of your sale. Might be worth looking into if you're facing a significant tax increase.

Based on all the helpful responses here, it sounds like you're unfortunately stuck reporting this on your 2024 taxes since the closing date determines the tax year, not when you received funds. But don't panic yet! There are still some strategies you can use to minimize the tax hit: 1. **Tax loss harvesting**: As Isabella mentioned, you can sell losing investments before Dec 31st to offset your gains dollar-for-dollar. Even if you don't have enough losses to completely offset the gains, every bit helps. 2. **Double-check your depreciation recapture calculations**: Make sure you're calculating this correctly - sometimes there are errors that can save you thousands. 3. **Consider installment sale treatment**: If any part of your sale proceeds are being paid over time (like seller financing), you might be able to spread out the tax impact. 4. **Opportunity Zone investment**: Omar's suggestion could defer these gains to 2026, which might solve your immediate bracket problem. I'd also recommend getting that Form 1099-S that Ravi mentioned - it will show exactly what date the IRS expects you to report this sale. And definitely follow up with your accountant ASAP since time is running out for any year-end tax planning moves. Good luck!

Had this exact issue. Called IRS after 4 weeks. They confirmed check was actually mailed. Started payment trace. Check arrived next day. Sometimes system updates before physical mailing occurs. Be patient. Almost there. Keep checking informed delivery.

Has anyone else noticed that the IRS seems to say checks are "mailed" before they actually hand them over to USPS? My refund was supposedly mailed on February 24th but didn't arrive until March 18th! I checked informed delivery every single day and was getting so anxious. Should I call them to ask what's happening? What if it got lost? How long should I wait before panicking?

10 One additional consideration - the insurance company might allow your brother to "disclaim" a portion of the benefit, which would then potentially pass to contingent beneficiaries if any were named. Or they might allow a beneficiary to direct payment to multiple parties even if they're the only named beneficiary. Worth asking the insurance company directly about these options before the payout happens. I worked in insurance for years and companies often have procedures for these situations that aren't immediately obvious.

I'm sorry for your loss. This is a really tough situation to navigate during an already difficult time. One thing I'd suggest is asking MetLife to do a thorough search of their records for any communication from your mom about updating beneficiaries. Sometimes paperwork gets misfiled or processed under different policy numbers. They should be able to check if there were any phone calls, emails, or partial submissions that might support her intention to add you and your sister as beneficiaries. Also, depending on your state, there might be specific laws about how life insurance proceeds are handled when there's evidence of the policyholder's intent to change beneficiaries. Some states have provisions for "substantial compliance" where even incomplete beneficiary change attempts can be honored if there's clear evidence of intent. I'd recommend consulting with an estate attorney in your state who can review the specific facts and advise whether there are any legal options to pursue before defaulting to the gift tax approach. The consultation might cost a few hundred dollars but could potentially save thousands in taxes and complications down the road.