I do have email correspondence outlining the scope of work and agreed payment terms, but not a formal signed contract. She sent me spreadsheets tracking which returns I completed and amounts owed, which I've saved. Would these be sufficient documentation for a small claims case? I'm in Texas, which I believe doesn't have a specific tax preparer regulatory board, but I'll definitely look into state-specific options.

Email correspondence can absolutely serve as documentation of your agreement, especially if it clearly outlines the work to be done and the payment terms. Those spreadsheets tracking completed returns will be particularly valuable evidence. For small claims court in Texas, you'd want to compile all communications about the work, evidence that you completed the work (like submission confirmations or acknowledgments from her that she received the completed forms), and documentation of any partial payments already made. Texas small claims (Justice Court) has a limit of $20,000, so your claim would fit well within their jurisdiction.

Really good point. Maybe OP should start by sending a message formally stating they still have access to all these sensitive business details through the shared drive and requesting guidance on proper deletion once payment is received? That creates a paper trail showing they're trying to handle the info responsibly.

Is there an easy way to separate these out? My property tax bill has the base amount plus like 4 different "special assessments" for things like schools and flood control. Are those considered part of the deductible property tax?

Generally, special assessments for schools, flood control, and similar public improvements are deductible as property taxes as long as they're based on the assessed value of your property and apply to all properties in the jurisdiction. However, special assessments for local benefits that increase the value of your property (like sidewalks, streets, or water/sewer lines specifically for your neighborhood) are not deductible as taxes. The easiest way to separate these is to look at your property tax statement - it should itemize the different charges. If you're using tax software, it will usually ask you to enter only the deductible portions. Or if you work with a tax professional, they'll know how to properly categorize each item.

It really depends on your total itemized deductions. Remember that itemizing includes property taxes, state/local income taxes (capped together at $10k), mortgage interest, charitable contributions, and some medical expenses. If all those combined exceed your standard deduction, then itemizing is worth it. But you're right that the higher standard deduction has made itemizing less beneficial for many homeowners.

That's interesting. I didn't have any extreme circumstances like that though. Just poor planning and procrastination on my part unfortunately. Do you know if the IRS ever just "forgives" these situations if I explain it was an honest mistake?

The IRS generally doesn't "forgive" missed deadlines just because it was an honest mistake. They hear that all the time. If it was truly just procrastination, you'll need to follow the pay-first-then-claim-refund route the others mentioned. However, there was actually a recent Supreme Court case (Boechler v. Commissioner) that established equitable tolling could apply for certain tax deadlines, though that was for Collection Due Process cases, not deficiency notices. Still, tax law continues to evolve on these issues.

In my experience, amended returns are taking FOREVER right now - like 6+ months. I filed one in April and it's still "processing" according to Where's My Amended Return tool. But that's separate from the Tax Court deadline issue. The amended return won't stop the deficiency assessment if you missed the petition deadline.

Yes! I just double-checked and found it in the supplemental pages! There's a whole separate section for "Proceeds from Broker and Barter Exchange Transactions" that has all the info I need, including acquisition date and cost basis. Thanks for pointing this out - I was only looking at the first page.

Glad you found it! Robinhood's tax documents can be confusing because they combine different forms into one package. That supplemental section is actually the most important part for crypto transactions since it contains all the details you need for Form 8949. Just make sure you're using the correct acquisition dates since that determines whether it's long-term or short-term capital gains.

Yep, happened to me too. The cost basis on my 1099-B was off by about $25 compared to what my actual purchase price was. I had to file a Form 8949 with code B to indicate the cost basis was reported incorrectly to the IRS.

Thanks for bringing up the look-back rule - I hadn't considered that! I do have a small 1231 loss from a property I sold in 2023. So if I understand correctly, a portion of my current gain would be considered ordinary income rather than capital gain? Would that portion not be eligible for OZ investment?

Yes, exactly. If you had a 1231 loss in 2023, a portion of your current 1231 gain would be recaptured as ordinary income to the extent of that previous loss. That recaptured portion would not be eligible for OZ investment, since OZ investments can only be made with capital gains. For example, if you had a $10,000 1231 loss in 2023 and now have a $50,000 1231 gain, $10,000 of your current gain would be treated as ordinary income and only the remaining $40,000 would be treated as capital gain eligible for OZ investment.

I invested in an OZ fund after selling a small apartment building in 2022. The fees are definitely higher than typical investment funds, but remember you're getting tax benefits that can offset those costs. I went with a fund focused on multifamily development in emerging markets which aligned with my investment goals. Make sure you do due diligence on the fund manager's track record and understand the timeline - you need to hold for 10+ years to get the full tax benefits on appreciation. And be prepared for the tax bill in 2026 on your initial deferred gain.