That distinction makes a lot of sense, thank you! In my case, I paid for a specific procedure that was scheduled for the following year, so it sounds like I can deduct it on my 2022 taxes. And yes, even with this expense added, my medical costs will be about 9.2% of my AGI for 2022, so I should benefit from the deduction. I'm definitely itemizing because my mortgage interest and state taxes already put me well over the standard deduction amount.

Do credit card statements count as proof of payment date? I have a lot of medical expenses but didn't keep all the paper receipts.

Credit card statements are definitely helpful as proof of payment date, but the IRS typically wants more detailed documentation too. You should try to get copies of the actual receipts or invoices from the medical providers if possible - most offices can reprint them even from previous years. The credit card statement shows you paid something on a certain date, but doesn't prove what specific medical service it was for. Having both the credit card statement AND the detailed receipt/invoice creates a much stronger paper trail if you ever get audited.

I use TurboTax and for this situation, you'd just enter the full rent amount as income on Schedule E, then add the value of services (like lawn mowing) as a separate expense under "repairs and maintenance" or whatever category is appropriate. TurboTax doesn't have a specific field for "payment in kind" - you just handle each side of the transaction separately.

This is such great advice about keeping detailed records! I'm just getting started as a landlord and hadn't thought about the documentation aspect. When you say you track the "fair market value" of services, how do you actually determine that? For example, if my tenant agrees to do landscaping work, do I need to get quotes from landscaping companies to establish the value, or is there a simpler way to document it? Also, your point about tracking utilities as both income and expense makes total sense now. I was getting confused trying to figure out the "net" effect, but separating them out seems much cleaner for record-keeping purposes.

Thank you all for the helpful information! I will wait until April 9th (4 weeks) before taking further action. I didn't know there was such a big gap between when they say it's mailed and when it actually arrives.

@Miranda Singer Your timeline is actually pretty typical unfortunately! The 3+ week delay you experienced matches what many of us have been seeing this tax season. The IRS mailed "date" seems to be when they approve it for Treasury processing, not when USPS actually gets it. I d'suggest waiting the full 4 weeks before calling - that seems to be the magic number when they ll'actually help you start a trace. The anxiety is totally understandable though, especially when you re'expecting it and checking informed delivery daily!

This is excellent advice about the contemporaneous documentation requirement. I'm curious - what happens if someone has kept all their losing tickets but didn't maintain a detailed gambling diary at the time? Are they completely out of luck, or is there a way to reconstruct acceptable records after the fact? Also, you mentioned consulting with a tax professional who specializes in gambling income. How do you find someone with that specific expertise? Most CPAs I've talked to seem to have limited experience with large gambling winnings and losses. Given that the original poster has $180k in winnings, do you think the IRS automatically flags returns with gambling income above a certain threshold, or is it more about unusual patterns in the deductions claimed?

Great questions! If someone only has losing tickets without a contemporaneous diary, they're not completely out of luck, but they're in a much weaker position. The IRS may still accept the tickets as evidence, but they'll want to see supporting documentation like bank records, credit card statements, or casino player's club records that show the pattern of gambling activity. You can try to reconstruct records using these financial documents, but it's much less reliable than having kept proper records from the start. For finding a CPA with gambling expertise, look for Enrolled Agents (EAs) or CPAs who advertise experience with "gaming industry" or "professional gamblers." The American Institute of CPAs has a directory where you can search by specialty. Tax attorneys who work with casinos or professional poker players are another option, though more expensive. Regarding IRS flagging, large gambling winnings often trigger automatic review because of the W-2G forms casinos and lottery commissions file. The IRS computer systems look for discrepancies between reported winnings and claimed losses. A $180k win with $180k in losses might raise questions simply because it's unusual for losses to perfectly match winnings. Having detailed, contemporaneous records becomes even more critical at these amounts.

This is really helpful advice about organizing documentation! I'm new to dealing with gambling winnings and this whole thread has been eye-opening. One thing I'm wondering about - you mentioned the difference between "session" losses and "annual" losses. Could you explain that a bit more? I'm not sure I understand what the IRS is looking for there. Also, regarding the AMT implications you brought up - is there a general threshold where AMT becomes a concern, or does it depend on your specific tax situation? With the amounts the original poster is dealing with, it sounds like getting professional help is definitely the way to go, but I'd love to understand the basics of when AMT might kick in. Thanks for sharing your knowledge - this stuff gets complicated fast!

Great question about the order! Generally, it's most tax-efficient to withdraw Roth contributions first since they're always tax and penalty free. Then for the remaining funds you need, you'll want to compare the tax impact of using the $10k exemption on Roth earnings vs traditional IRA funds. With Roth earnings under the exemption, you avoid the 10% penalty but may still owe taxes if you haven't met both the 5-year rule AND the age 59½ requirement. With traditional IRA funds under the exemption, you avoid the 10% penalty but definitely owe income tax on the full amount. So if your Roth has satisfied the 5-year rule, using the exemption on Roth earnings would likely be more tax-efficient. But everyone's situation is different - factors like your current tax bracket, expected future income, and how much you have in each account type all matter. This might be worth running through a tax calculator or consulting with a tax professional to optimize your specific scenario.

This is really helpful advice about timing! I hadn't thought about the "seasoned funds" issue with lenders. Quick question - when you say you had to keep the money in savings for 6 weeks and it complicated your application, did your lender ultimately accept it once you showed the paper trail? Or did you have to provide additional documentation to prove the source of funds was legitimate? I'm worried about creating unnecessary hurdles in an already stressful process.