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?

That's helpful, thanks! I moved October 10th and was in the US until December 18th when we returned for the wedding. We stayed in Canada until January 2nd, so that's about 27 days total in Canada for 2024. Sounds like I should be well under the 183-day threshold. Do pre-move days count toward this calculation too? Like, I was obviously in Canada from January-October before moving.

Yes, all days physically in Canada during the calendar year count toward the 183-day threshold, including January-October before your move. So you'd have roughly 9 months plus 27 days, which would put you over the 183-day threshold for 2024. However, this doesn't automatically make you a resident for the whole year. The CRA can recognize a change in residency status during the year. For people leaving Canada, they often consider you a part-year resident up to your departure date if you've legitimately established non-residency after that point. This is why your accountants are focusing on your ties after October, because they're trying to determine if you successfully established non-residency upon your departure.

I'd be careful with NR73. It can be helpful but it's also known to trigger extra scrutiny. My cross-border tax specialist advised against filing it unless absolutely necessary because it essentially puts you on CRA's radar and can lead to additional questions and reviews. Sometimes it's better to take a reasonable position based on your facts and circumstances and be prepared to defend it if questioned, rather than proactively asking for a determination.

Thanks for mentioning this! I had no idea there was a separate credit. Does this replace the medical expense deduction or can I potentially use both? Also, does it matter that I'm not physically taking care of her myself (since she's in a facility)?

You cannot double-dip by claiming the same expenses for both the Dependent Care Credit and as medical expense deductions. You'll need to choose which is more beneficial based on your overall tax situation. Generally, credits are more valuable than deductions, but it depends on your specific numbers. The good news is that you don't need to physically care for her yourself to claim the Dependent Care Credit. Expenses paid to a care facility qualify as long as part of the expense is for the care of your mom. However, if the facility provides medical care, you need to separate out the cost of care from the medical expense portion if you want to use both benefits for different expenses.

Is there any way to fix this if you've already been giving the money to the parent? My sister and I deposit money in our dad's account and he pays his care facility.

Does specific identification actually save you money compared to FIFO? And how exactly do you indicate which specific coins you're selling when you execute a transaction? It's not like stocks where you can pick specific shares.

Specific identification can potentially save significant money compared to FIFO, especially if you've bought the same cryptocurrency at very different price points over time. It allows you to strategically "sell" the lots with the highest cost basis first, minimizing your reported gain. You don't need to specify which coins you're selling at the time of the transaction. What matters is your accounting method and documentation. You need to maintain clear records showing the date and time each unit was acquired, your cost basis, the date and time of sale, and the proceeds. This becomes your evidence for using specific identification. Most specialized crypto tax software can help maintain these records and will let you choose which method to apply when generating your tax forms.

The IRS clarified in 2019 that like-kind exchanges (Section 1031) were never applicable to cryptocurrency trades, even before the 2018 tax law change that explicitly limited 1031 exchanges to real estate. Unfortunately, those 2017 crypto-to-crypto trades were taxable events. If you haven't been reporting them correctly, you might want to consider filing amended returns for those years. The statute of limitations is typically 3 years, but it can be extended in certain cases, especially if the IRS considers it substantial underreporting.

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.