Thanks for bringing up the look-back rule - I hadn't considered that! I do have a small 1231 loss from a property I sold in 2023. So if I understand correctly, a portion of my current gain would be considered ordinary income rather than capital gain? Would that portion not be eligible for OZ investment?

Yes, exactly. If you had a 1231 loss in 2023, a portion of your current 1231 gain would be recaptured as ordinary income to the extent of that previous loss. That recaptured portion would not be eligible for OZ investment, since OZ investments can only be made with capital gains. For example, if you had a $10,000 1231 loss in 2023 and now have a $50,000 1231 gain, $10,000 of your current gain would be treated as ordinary income and only the remaining $40,000 would be treated as capital gain eligible for OZ investment.

I invested in an OZ fund after selling a small apartment building in 2022. The fees are definitely higher than typical investment funds, but remember you're getting tax benefits that can offset those costs. I went with a fund focused on multifamily development in emerging markets which aligned with my investment goals. Make sure you do due diligence on the fund manager's track record and understand the timeline - you need to hold for 10+ years to get the full tax benefits on appreciation. And be prepared for the tax bill in 2026 on your initial deferred gain.

Thanks for the reminder about the Section 199A deduction! Is that handled automatically through Form 8995A or do I need to do something else to claim it? For the HSA, I'm contributing the maximum for individual coverage. One question though - if I switch to family coverage mid-year, can I contribute the full family amount or is it prorated?

Form 8995A is specifically for calculating your Section 199A (Qualified Business Income) deduction, so no need to do anything additional. It flows automatically to your 1040. For HSA contributions after switching to family coverage mid-year, it gets a bit complicated. You can actually contribute the full family maximum ($8,300 for 2024) if you're still covered by a family HDHP on December 1st and remain covered for the full calendar year of 2025 (called the "last-month rule"). If you don't maintain coverage through December 2025, you'd need to prorate your contribution based on how many months you had each type of coverage.

Just a quick correction - the SE tax is actually 15.3% (12.4% Social Security + 2.9% Medicare) on that 92.35% of net earnings, up to the Social Security wage base limit ($168,600 for 2024). Then 2.9% Medicare tax continues beyond that with no limit, plus an additional 0.9% for high earners. But your point about deducting half on Schedule 1 is super important - loads of people miss that and it's a significant deduction!

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.

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.