Wait, that sounds exactly like what might have happened! How did you resolve it once you realized the mistake? Did you have to file an amended return or just explain it in a response to their letter?

I didn't need to file an amended return. I sent a formal response to the IRS letter that included a new correctly filled out Form 8949 with the proper checkbox marked, along with documentation showing my actual purchase prices and dates for the Doge. I also included a brief letter explaining that I made an error in checking the wrong box but that I had in fact reported all income properly. They accepted my explanation and adjusted the amount owed to match what I had originally calculated and paid. The whole process took about 2 months from when I sent my response to getting their confirmation.

Do you know if they're focusing only on the major exchanges like Robinhood and Coinbase, or are they somehow tracking DeFi transactions too? I did some swaps on Uniswap back then that I'm not sure I documented properly.

Do you think it's better to use Section 179 or regular depreciation for something like a $3,000 computer? I've heard mixed advice about this.

It really depends on your overall business situation. If you're profitable this year and could use the deduction now, Section 179 gives you the immediate write-off which is great for cash flow. If you expect to make more money in future years, regular depreciation might make more sense to spread the deductions across years when you might be in a higher tax bracket. For a $3,000 computer, the difference might not be huge unless you're right on the edge of a tax bracket. I usually recommend taking the deduction now if your business can use it, since the time value of money means a deduction today is worth more than the same deduction spread over 5 years.

Unfortunately, no. You can only begin depreciation or take Section 179 when the equipment is "placed in service" - meaning it's in your possession and ready for use in your business. Paying a deposit doesn't count.

That's really helpful - I hadn't even considered the QBI deduction. Do you know if there are any special requirements for short-term rentals to qualify for this? And would taking the QBI deduction affect my ability to offset losses against W2 income in any way?

For short-term rentals to qualify for the QBI deduction, they need to rise to the level of a "trade or business" under Section 162, which generally means regular, continuous, and substantial activity - which your hands-on management would likely satisfy. The IRS also issued Revenue Procedure 2019-38 which provides a safe harbor specifically for rental real estate activities. Taking the QBI deduction doesn't affect your ability to offset losses. They're completely separate concepts. If your rentals show a net loss in a given year, there's no QBI deduction to take (since it's calculated on profits). But in profitable years, you'd potentially get both the regular business expense deductions and the additional QBI deduction on what's left.

Agreed about documentation. My friend got audited on exactly this issue and the IRS disallowed their short-term rental losses because they couldn't prove they met the material participation hours. Keep a calendar or app with dates, times, and descriptions of all activities.

I haven't tried FreeTaxUSA yet! Does it have a good interface? My biggest frustration with some of the smaller tax services is that the UI feels like it was designed in 1997 lol.

The interface isn't as fancy as TurboTax or H&R Block, but it's definitely not from the 90s! It's clean and straightforward, just without all the animations and excessive hand-holding. Everything is organized logically and I actually find it faster to use than the big name services. They're especially good with 1099-NEC and other self-employment forms since you don't get routed into "upgrade now!" pages halfway through. Their help content is also surprisingly detailed if you get stuck on something.

I found a workaround last year! If you go through the IRS Free File portal instead of directly to the tax service website, some of them are required to give you the free version even with 1099-NEC forms. There's an income limit though.

Thanks for this suggestion! My dispute is actually for about $45,000 so this would apply to me. Do you know if filing this way still preserves all my rights if I later decide to get an attorney involved? And does the simplified procedure still allow the examiner to continue working on my case?

Yes, filing under the simplified procedure (S case) still preserves your rights. The main difference is that S cases have a more informal process and you can't appeal the decision beyond the Tax Court. But that's rarely an issue since most cases settle before trial anyway. And absolutely, the examiner can still continue working on your case even after you file. In fact, once you file the petition, your case gets assigned to an IRS attorney who will often work with your examiner to try to settle the case quickly rather than going to trial. Many people find that filing the petition actually speeds up resolution because it puts time pressure on the IRS to wrap things up.

And make sure to send it CERTIFIED mail with return receipt if you're mailing it! That way you have proof of when you sent it in case there's any question.