Thank you so much for sharing your experience! Did your WMR tool update before the deposit hit your account? Mine still shows the first bar even though the transcript has the 570 code.

The WMR tool hardly ever updated correctly for me. It was still showing "return received" even after my refund was deposited! The transcript is much more accurate and reliable than WMR. If you check your transcript again in a week or so, you'll probably see the 571 code pop up, followed by code 846 with your refund date. That's the real indicator to watch for.

Does the hold still apply if you're only claiming a small EITC amount? I only qualified for about $340 in EITC this year, but my total refund is over $3,000 from withholding. Seems silly to hold the entire amount for such a small credit.

What happened after you got hit with the tax bill? Did you ever try to get it corrected or did you just pay it? I'm in a similar situation but with a restaurant that closed down, so I'm not even sure if the owner is still around to issue a corrected form.

I ended up paying it the first year because I didn't know any better. The second year, I filed the SS-8 form proactively and got a determination letter from the IRS saying I was indeed an employee. I took that to the owner, who initially resisted but changed his tune when I mentioned the potential penalties for misclassification. He issued a corrected W-2 for that year. For the previous year, I filed an amended return with the determination letter and got about $1,600 back. Even if your restaurant closed, you can still file the SS-8 and possibly get a determination that helps with your taxes. The owner being gone doesn't prevent the IRS from making a ruling on your status.

Getting paid through Cash App doesn't determine your worker status - that's based on the nature of your working relationship. However, you're right about the reporting change. Cash App (and similar payment services) are required to issue 1099-Ks for accounts receiving over $600 in payments for goods and services. This is separate from whether your employer issues a 1099-NEC or W-2. The IRS may notice if you receive a 1099-K from Cash App but don't report that income, regardless of whether you also get a 1099 or W-2 from the employer. So the income definitely needs to be reported either way, but the classification as employee vs. contractor determines HOW you report it and how much tax you pay.

Thanks for explaining! So if I'm understanding right, I could potentially get both a 1099-K from Cash App AND either a 1099-NEC or W-2 from my employer for the same income? That seems like it would cause confusion with the IRS. How would I make sure I'm not double-reporting the same income?

This is extremely helpful, thank you! One question - when creating this transaction log, should I calculate the USD value of the BTC at each transfer point? Or just focus on the final gain/loss numbers?

Yes, you should definitely record the USD value of the BTC at each transfer point. This is crucial because the IRS considers each crypto-to-fiat or crypto-to-crypto exchange a potentially taxable event, and those values establish your cost basis. When you transfer BTC to your forex broker and convert to fiat, you technically have a taxable event based on whether your BTC gained/lost value since purchase. Then your forex trading creates separate taxable events. Finally, when converting back to BTC, there's another taxable event. Recording the USD values at each step creates a clear audit trail that properly separates the crypto transactions from the forex transactions.

Forex trades under Section 988 (which is the default for most retail forex traders) are NOT subject to wash sale rules. They're treated as ordinary income/loss rather than capital gains/losses. However, if you elected to use Section 1256 treatment (which most retail traders don't), then different rules would apply. Make sure you're consistent in your treatment though. You can't cherry-pick which trades fall under which section to maximize tax benefits.

Thanks for clearing that up! I've definitely been treating everything as Section 988 since I'm doing short-term day trading, so I should be good. I'll override the flag in my tax software and make a note explaining that these are forex trades under Section 988 and therefore exempt from wash sale rules.

Can I deduct Spotify if I use it to play music for open houses? Or is that stretching it?

That's actually a good question about Spotify. If you're using it exclusively for business purposes like open houses, you might be able to deduct it. However, if you also use it personally (which most people do), you would need to determine what percentage is for business use and only deduct that portion. Generally speaking, you need to be careful with these "dual-use" subscriptions. The safest approach would be to keep track of how many hours/days you use it specifically for open houses compared to personal use. But honestly, for something relatively small like a Spotify subscription, the record-keeping burden might outweigh the tax benefit.

This is such an important point! My friend went through this exact situation and ended up with a big tax bill because the broker wasn't withholding taxes. What questions should OP ask to make sure they're properly classified?

Did you find any good way to automate the collection of exemption certificates? We're struggling with getting schools to promptly provide their exemption documentation, and it's creating a bottleneck.

We built a simple upload portal as part of our onboarding process where organizations couldn't list events until they uploaded their exemption certificates. We also created state-specific templates with instructions that made it easier for them to provide exactly what we needed. For schools specifically, we found that being very clear about the consequences of not providing documentation (i.e., we'd have to charge their students/parents sales tax) motivated them to respond faster. Most schools already have these certificates on file, so it's just a matter of getting the right person to share them.

Great question about physical presence. While marketplace facilitator laws create nexus for the online sales portion, the physical location of events can indeed trigger additional tax considerations. In some states, there might be amusement taxes, entertainment taxes, or special venue taxes that apply based on where the event physically takes place. These are separate from sales tax on the tickets themselves and may have different filing requirements.