Does CashApp Taxes handle cryptocurrency transactions? I did a bit of trading last year along with my regular job and some freelance work, so I need something that can deal with all of that.

CashApp Taxes has basic support for cryptocurrency transactions, but it's somewhat limited. You'll need to enter your transactions manually or import a summary from your exchange. For more complex crypto situations with lots of trades, you might want a more specialized solution. For your combination of W-2, freelance, and crypto income, TaxAct might actually be the better choice. Their crypto reporting tools are more robust and they integrate with several popular crypto exchanges for easier importing. They've really improved their crypto support over the last couple years as it's become more common.

Have you ever had your return audited using OLT? I'm always worried the cheap options might miss something or not be as thorough.

Just checked out OLT - that price is insane! But their website looks super dated. Does it handle Schedule C for self-employed people well? And how's the user experience? I don't mind basic interface if it works properly.

This is super helpful, thank you! How long did it take them to respond to your abatement request? And did you have to provide any specific evidence beyond just pointing out the timeline?

It took about 6 weeks to get a response, which was actually faster than I expected. I didn't need special evidence beyond clearly outlining the timeline with specific dates. One tip - I made sure to include all the reference numbers from the CP2000 notice at the top of my letter and made it very clear I wasn't disputing the actual adjustment, just the interest. I think that helped it get processed faster since they knew I wasn't challenging the underlying tax assessment. I also kept it to one page and very factual - no emotional language about how unfair it was. Just dates, facts, and the specific tax code.

I tried the Taxpayer Advocate last year for a similar issue but they told me they couldn't help because it wasn't an "economic hardship" situation. Seems like they're really only equipped to help if you're facing immediate financial difficulty, not just regular interest disputes. Worth a shot I guess but they're also super backed up these days.

Good point about the hardship requirement. I think my situation qualified because I was facing a lien at the time. For regular interest issues, probably better to go with the interest abatement request directly to the IRS like others mentioned. The Taxpayer Advocate is really more for when you're truly stuck in the system or facing serious consequences.

Does the timing issue apply differently for Roth vs Traditional IRAs? I have a similar situation with both types of accounts and I'm confused about which deadlines apply to each.

The timing rules are actually the same for both Roth and Traditional IRAs. For both types, you need to withdraw excess contributions (and any earnings on those contributions) by your tax filing deadline including extensions (typically October 15th) to avoid the 6% excise tax penalty. The main difference is in how the earnings are treated. For Traditional IRAs, the earnings are generally taxable in the year you make the withdrawal. For Roth IRAs, the earnings are also taxable if you withdraw them, but they may additionally be subject to the 10% early withdrawal penalty if you're under 59½ and don't qualify for an exception.

Yes, you'll likely need Form 5329. I had a similar situation and had to use it to report the excess contribution and show that I had taken corrective action by removing it, even though it was incorrectly coded as a normal distribution. This helps avoid the 6% excise tax on excess contributions.

They just remove the money and any associated earnings - they don't close your account. I had this exact situation with Vanguard last year, and my account stayed open with a $0 balance after the removal.

Would this work for crypto? I've got some ETH that's gone up like crazy and I'm trying to figure out how to cash some out without giving half to Uncle Sam.

Yes, it can work for cryptocurrency. The key is that the trust sells it after you've donated it, so the trust itself doesn't pay capital gains tax on the appreciation. You'll need to find a trustee comfortable with handling crypto assets though, as some traditional trustees aren't familiar with the process. Keep in mind that you're ultimately giving a portion to charity - this isn't a strategy to avoid taxes completely while keeping all the money. But the tax benefits plus the income stream can make the math very favorable compared to just selling and paying capital gains tax directly.

I looked into something similar for my business. The Wyoming LLC part can work for privacy and some liability protection, but it doesn't magically change your tax situation. The IRS follows the money regardless of how many entities you put in between. And trying to loan yourself money through your own entities gets really tricky really fast.