Has anyone used appeals after getting a Notice of Deficiency? I know typically you'd go through appeals before getting a NOD, but in my case, the revenue agent went straight to issuing the notice without giving us a chance at appeals.

I've been through a similar situation and wanted to share what worked for us. We received a Notice of Deficiency for $31,000 in disallowed business expenses, and honestly, the 90-day deadline felt overwhelming at first. Here's what I learned: Don't wait to file the Tax Court petition if you believe the IRS is wrong. Filing the petition doesn't mean you're committing to a full trial - it preserves your rights and stops the assessment clock. Many cases get resolved through settlement conferences with IRS Appeals once you're in the Tax Court system. The key is having your documentation organized and a clear argument for why each expense should be allowed. We ended up settling for about 20% of the original assessment without ever going to trial. The IRS Appeals officer was much more reasonable to work with than the original examining agent. Also, consider getting professional help if the amount is significant. The cost of a tax attorney or CPA experienced with Tax Court cases is often worth it when you're dealing with a $24,000+ assessment. They know exactly how to present your case and what Appeals officers are looking for in settlement discussions. Time is your enemy here - use it wisely to build the strongest case possible rather than hoping for a miracle solution that avoids Tax Court entirely.

One important thing nobody mentioned - you need to track your expenses CAREFULLY! I made this mistake my first year of selling handmade stuff. Just because PayPal only reports income over $600 doesn't mean you can't deduct your legitimate business expenses. Save receipts for EVERYTHING related to your digital design work. Software, hardware, portion of internet bill, even a percentage of your electricity if you work from home. These deductions can often bring you below the $400 threshold where you'd need to pay self-employment tax. I learned this the hard way!

Another thing to consider is quarterly estimated tax payments. If you expect to owe more than $1,000 in taxes for the year, you're supposed to make quarterly payments instead of paying it all when you file your return.

Has anyone dealt with a situation where one heir wants to buy out the other after a partial step-up? My brother and I inherited our parents' vacation home (50% each, at different times), but now he wants to sell his half to me. We're struggling to figure out the right price since we have different tax basis amounts.

This is exactly the kind of situation where proper planning can save your family tens of thousands in taxes. You're absolutely right to avoid the lifetime gift route - that would be a costly mistake. One thing I'd add to the excellent advice already given: make sure your uncle's estate planning documents are crystal clear about bypassing his spouse for the property transfer. Depending on your state, there could be spousal elective share issues that complicate things if not handled properly in his will or trust. Also consider having a family meeting now to discuss what happens if either you or your cousin wants to sell their share later, or if one of you can't afford the ongoing property taxes and maintenance. It's much easier to agree on buy-sell arrangements while everyone is getting along than after emotions and money stress get involved. The stepped-up basis approach you're planning is definitely the right move tax-wise. Just make sure all the legal paperwork supports that plan.

Anyone else find it ridiculous that a $1.50 wash sale forces you to potentially list dozens of transactions individually? The tax code is so user-unfriendly sometimes.

I went through this exact same situation last year with TurboTax and a small wash sale from my E*TRADE account. The good news is you definitely don't need to enter all 40+ transactions individually! Here's what I learned: you can use a hybrid approach where you summarize all the "clean" transactions (the ones without wash sales) on one line of Form 8949, then separately list only the specific transactions that had wash sales with the "W" code. So if you have 40 transactions and only one or two involved wash sales, you'd have maybe 2-3 lines total on your Form 8949 instead of 40+. The summary line covers all the normal trades, and then you have individual lines for just the wash sale transactions. FreeTaxUSA should handle this - when you're entering your transactions, look for options to "summarize" or "aggregate" the regular ones, then add the wash sale transactions separately. Make sure the wash sale entries include the adjustment amount from your 1099-B in column (g). Don't let that tiny $1.50 wash sale force you into hours of data entry!

If you filed your 2019 taxes electronically through H&R Block, you could try requesting your tax transcript directly from the IRS instead of dealing with H&R Block customer service. Go to IRS.gov and search for "Get Transcript Online" - you can download most tax records immediately.

I went through this exact same nightmare with H&R Block earlier this year! What finally worked for me was filing a complaint with the Better Business Bureau. I know it sounds dramatic, but within 48 hours of filing the complaint, I got a call from H&R Block's executive customer service team who immediately helped me access my missing returns. The regular customer service line is absolutely useless - I spent probably 6 hours total on hold over multiple days. But once I escalated it through the BBB, they took it seriously. The executive team member was able to access my archived returns right away and emailed them to me as PDFs within an hour of our call. It's ridiculous that it takes a formal complaint to get basic customer service, but if you're desperate and need those documents quickly, this route actually works. The BBB complaint is free to file online and you'll get a response much faster than waiting for their regular support.