Don't forget you need to keep records showing you actually PAID those amounts too! I got audited in 2021 and they wanted to see both the EOB AND proof I paid the amount (bank statement, credit card statement, etc). The EOB just shows what you OWED, not necessarily what you PAID.

Great question! EOBs are definitely acceptable documentation for HSA reimbursements. I've been managing my HSA for years and have used EOBs successfully during IRS correspondence audits. The key thing to remember is that your EOB needs to clearly show: - Date of service - Type of service (prescription drug, medical service, etc.) - Provider information - Amount you were responsible for paying Most insurance EOBs include all this information. Just make sure you're only reimbursing the patient responsibility amount (what you actually paid out-of-pocket), not the total billed amount. One tip: if your EOBs don't clearly show the medication names, you might want to supplement with a brief note in your records about what the prescription was for, just in case. While not strictly required, it can help if questions arise later. Keep those EOBs for at least 7 years - electronic copies are fine. The IRS doesn't require paper documentation, so PDFs from your insurance portal work perfectly.

This is exactly the kind of situation where having a good relationship with your CPA becomes crucial. I went through something similar last year and learned that most experienced tax professionals have templates and procedures specifically for trust short-year returns. One approach that worked well for me was to schedule a planning meeting with the CPA about 60 days before the intended termination date. We created a detailed timeline that included: requesting preliminary statements from all financial institutions, identifying any potential late-arriving income sources (like partnership K-1s), and calculating estimated tax reserves. The key insight my CPA shared was that the IRS is generally reasonable about good-faith estimates on short-year returns, especially for trusts. As long as you document your methodology and show that you made reasonable efforts to capture all income, minor discrepancies usually aren't problematic. Also consider the timing of your termination date strategically - if you terminate right before a major dividend payment date, you might avoid having to estimate that income entirely. My CPA helped me identify the optimal termination timing based on the trust's specific investment holdings.

As someone who recently went through this exact process, I can't stress enough how important it is to start gathering your preliminary financial statements early. I made the mistake of waiting until the last minute and discovered that one of our brokerage firms needed 10 business days to generate the year-to-date report. Here's what I wish I had known earlier: create a comprehensive asset inventory first, then systematically contact each institution about 6-8 weeks before your planned termination date. For investment accounts, ask specifically for "income and realized gains/losses through [termination date]" rather than just a general statement - this ensures you get the tax-relevant information. Also, don't forget about any automatic reinvestment plans (DRIPs) that might generate small amounts of additional income right up until termination. These often get overlooked but can affect your final tax calculations. One last tip - if your trust has any money market accounts or CDs that will mature after your planned termination date, factor in that accrued interest when calculating your reserves. The preliminary statements often don't capture interest that's earned but not yet paid, which can create surprises later.

I dealt with a similar situation after Hurricane Laura damaged my roof and garage. One thing that really helped my case was getting a "scope of loss" document from a public adjuster who reviewed what my insurance company missed or undervalued. Even though I had to pay the adjuster, it was worth it because they found an additional $12k in damages that insurance initially overlooked. For your chimney situation, you might want to consider getting a structural engineer's assessment showing that removing the chimney versus rebuilding it creates a permanent decrease in your home's structural integrity and value. This could strengthen your FMV decrease argument beyond just the aesthetic/functional loss. Also, don't forget that you can deduct the cost of temporary protective measures you took immediately after the hurricane (like tarping, boarding up windows, etc.) as part of your casualty loss. These often get overlooked but they're legitimate disaster-related expenses. Just make sure everything was within a reasonable timeframe after the federally declared disaster.

I went through a very similar situation after Hurricane Michael hit our area. One crucial detail that hasn't been mentioned yet - make sure you understand the timing rules for casualty loss claims. Since yours was a federally declared disaster, you actually have the option to claim the loss on either your 2024 return (the year it happened) OR amend your 2023 return to claim it there, which could get you a refund faster. The key documentation you'll need beyond what others have mentioned is a detailed timeline showing when the damage occurred, when you received the insurance settlement, and when you made the decision to go with the wall replacement instead of full chimney rebuild. The IRS wants to see that you made reasonable efforts to restore the property but were financially unable to do so. For your specific situation with the chimney-to-wall conversion, I'd strongly recommend getting an appraisal or real estate professional's written opinion on how this impacts your home's resale value. A missing chimney can affect both the aesthetic appeal and functionality (no fireplace option for future buyers), which supports your FMV decrease calculation. One last tip - if you're planning to sell your home within the next few years, keep all this casualty loss documentation. It could affect your capital gains calculation since the casualty loss reduces your home's adjusted basis.

This thread has been incredibly valuable! As someone currently dealing with H&R Block errors (they somehow managed to file me as "married filing separately" when I'm single), I'm taking notes on everyone's strategies. One additional tip I'd add: if you paid by credit card, consider disputing the charge with your credit card company while you're pursuing other complaint channels. Under the Fair Credit Billing Act, you can dispute charges for services that weren't performed satisfactorily. I filed a dispute with my Visa card explaining that H&R Block's preparation was defective, and having that additional pressure point really got their attention. The credit card company temporarily credited my account while they investigated, which gave H&R Block extra incentive to resolve the issue quickly rather than risk losing the chargeback dispute. They ended up settling with me directly within 10 days to avoid the chargeback going through. Just make sure to dispute within 60 days of your statement date, and document everything for the credit card company just like you would for the other complaint channels. It's another tool in your arsenal that costs nothing to use!

This entire thread has been incredibly helpful! I'm dealing with a similar H&R Block nightmare where they completely botched my business taxes - missed obvious deductions and somehow calculated my quarterly payments wrong, leaving me with a huge unexpected tax bill. Reading through everyone's experiences, I'm amazed at how systematic you all got with your complaint strategies. I've been just randomly calling and getting nowhere, but now I see I need to be way more organized about this. I'm definitely going to try the taxr.ai analysis first to get concrete documentation of their errors, then use that multi-pronged approach several of you mentioned - BBB complaint, state AG, and the credit card dispute idea is genius! One thing I'm curious about - for those who got H&R Block to cover IRS penalties, did you have to wait until the IRS actually assessed the penalties, or were you able to get them to agree to cover potential penalties before they hit? I'm worried about timing since I know penalties can take months to show up, but I don't want to wait that long to file my complaints while the issues are fresh. Thanks everyone for sharing your experiences - this gives me hope that I can actually get this resolved instead of just eating the cost of their incompetence!

Don't forget about the Net Investment Income Tax (NIIT) of 3.8% that kicks in for investment income when your modified adjusted gross income exceeds $200,000 for single filers. With $105k in capital gains plus your other income, you might be approaching that threshold.

Congrats on the successful trades! Here are a few additional things to consider that haven't been fully covered: 1) **Estimated Tax Safe Harbor Clarification**: Since your prior year tax was $3,100, you need to pay at least 100% of that (not 110%) to avoid penalties, as the 110% rule only applies if your prior year AGI exceeded $150,000. Your $3,000 in quarterly payments gets you very close. 2) **Form 8949 Preparation**: Start organizing your trade data now. You'll need specific details for each transaction (date acquired, date sold, proceeds, cost basis) for Form 8949. Most brokerages provide this in a downloadable format. 3) **Estimated Tax for 2025**: Don't forget that you'll likely need to make much larger quarterly payments next year if you plan to continue trading. The IRS expects you to pay based on your current year's expected income. 4) **Record Keeping**: Document everything related to these trades - confirmations, statements, any fees paid. The IRS can audit investment income, and good records are essential. Since you mentioned being overseas, also verify that your trades don't trigger any FBAR (Foreign Bank Account Report) requirements if you used foreign brokerage accounts.