This is really helpful - I hadn't thought about the pass-through issue. In my case, the artists are receiving payment directly from their platforms and then sending me my percentage (usually 15-20%). So if they make $1000, they'd send me $150-$200 via Venmo. Does that simplify things since I'm only receiving my commission portion?

That definitely simplifies your situation! Since you're only receiving your commission portion directly, there's no pass-through income to worry about. The full amount you receive through Venmo is indeed your business income that should be reported on your Schedule C. Just make sure you're tracking each payment received with details on which artist it came from, what platform earnings it relates to, and the commission percentage applied. This documentation will help support your reported income if you're ever questioned. It's also smart business practice to send your artists an annual statement showing the total commissions they paid you, both for their records and yours.

This might be overkill for small payments though. I pay VAs in the Philippines less than $5k each per year and my accountant said as long as I have good documentation of the work performed and payments made, I don't need to worry about additional foreign reporting forms. Might depend on the dollar amount?

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.

Is there any advantage to using an FSA instead of an HSA for braces? I have both options at my work and never know which one to pick during open enrollment.

HSAs are generally better since the funds don't expire and you can invest them, but FSAs sometimes make sense if you know you'll have a large expense in that specific year. For braces specifically, one advantage of FSAs is that many allow you to access your full annual election amount at the beginning of the plan year, even before you've made all the contributions. So you could pay a large orthodontic bill in January but the money comes out of your paycheck gradually throughout the year.

That's really smart! Did you end up getting a decent tax refund from being able to deduct it? I'm trying to decide if it's worth all the hassle of tracking these expenses versus just using my HSA.

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.

Do you know if there's an easy way to figure out which tax treaty benefits apply? I've tried reading through the actual treaties and they're practically unreadable with all the legal jargon.

The IRS Publication 901 (U.S. Tax Treaties) provides summaries of the major provisions in each treaty in more understandable language. It's still dense reading, but much better than the treaties themselves. For a quicker reference, check the IRS website section on tax treaties where they have tables showing the reduced tax rates for different types of income based on country. However, these only cover basic situations, so for complex scenarios like your colleague's, it might be worth consulting with a tax professional who specializes in international taxation.

Did you have to file a separate 1040-NR for the nonresident part of each year? My accountant is telling me different things each time I ask.