Just wanted to add that I tried a similar strategy a few years ago with a BVI corporation for my trading activity. Ended up paying over $45,000 in penalties and back taxes when I got flagged for audit. The IRS agent told me they specifically look for US traders trying to route activities through Caribbean tax havens.

I've been researching similar offshore strategies for my trading business and I have to echo what others have said - the risks far outweigh any potential benefits. The IRS has really cracked down on these structures over the past decade. What changed my perspective was learning about the "economic substance doctrine" - even if you technically follow all the rules for setting up an offshore entity, the IRS can still challenge it if there's no legitimate business purpose beyond tax avoidance. For day trading, it's really hard to establish genuine economic substance in the Cayman Islands when you're sitting at your computer in the US making all the trades. I ended up working with a tax professional who specialized in trader tax status and found legitimate domestic strategies that actually reduced my tax burden more than I expected. Things like proper entity selection, maximizing business expense deductions, and qualifying for trader tax status can make a significant difference without the compliance nightmare and legal risks of offshore structures. The reporting requirements alone for foreign entities would probably cost you more in professional fees than you'd save in taxes, not to mention the constant worry about whether you're crossing the line into evasion territory.

Great thread! I'm also considering making the switch from H&R Block. Reading everyone's experiences really highlights how much value a good EA can provide beyond just filling out forms. One thing I'm curious about - for those who switched, how did you find your EA? Did you go through the IRS directory, get referrals, or use another method? I want to make sure I find someone with experience in small business situations like mine (freelance graphic design work plus rental property). Also, when you first met with your EA, what questions did you ask to evaluate whether they were a good fit? I don't want to make the same mistake of ending up with someone who just goes through the motions, even if they have better credentials than H&R Block preparers.

I made the switch from H&R Block to an EA last year and it was absolutely worth it. My situation was similar - W-2 income plus a growing freelance business and some investment income. At H&R Block, I felt like I was getting cookie-cutter service for $340, and when I asked about business deductions, the preparer seemed unsure and kept looking things up. My EA charges $525, but in the first year alone they found $2,900 in deductions H&R Block had missed - proper business use of vehicle calculations, home office deductions I qualified for, and equipment depreciation I never knew about. They also helped me set up a SEP-IRA which saves me thousands annually. The biggest difference is the ongoing relationship. My EA proactively reaches out with tax planning suggestions throughout the year. Last fall, they recommended some equipment purchases and retirement contributions that significantly reduced my tax burden. With H&R Block, it was always just a once-a-year transaction. One tip: interview a few EAs before choosing. Ask about their experience with your specific situation and whether year-round consultations are included or extra. The good ones will ask detailed questions about your business and suggest strategies right in the initial meeting.

Filed January 23rd, stuck in pending until February 6th (a full 14 days!), then magically accepted overnight. The IRS is moving slower than a sloth on vacation this year! 🐌 But seriously, I wouldn't worry yet. I meticulously track my tax timeline every year in a spreadsheet (yes, I'm that person 😂), and this is by far the longest pending-to-acceptance window I've seen. Just be cautious about making any major financial plans that depend on your refund arriving by a specific date - I'd add at least an extra 2-3 weeks to whatever timeline you're expecting based on previous years.

Filed on 1/26 and still pending here too! This is so frustrating - I've been a TurboTax user for 8 years and never experienced anything like this. Usually get accepted within hours like you mentioned. I called TurboTax support yesterday and they basically said "it's an IRS issue, not us" which wasn't helpful at all. The uncertainty is the worst part - at least if they told us "expect 3-4 weeks this year" we could plan accordingly. Instead we're all just checking obsessively every day wondering if something went wrong. Thanks for posting this - it's oddly comforting to know I'm not alone in this pending purgatory!

Something everyone's missing - if you win under like $600 at blackjack, the casino doesn't report it to the IRS so nobody would ever know if you didn't report it. Just saying... the IRS has bigger fish to fry than someone who won $270 playing cards lol

I just went through this exact situation last year! Won about $400 at a poker tournament and was totally confused about reporting it. Here's what I learned: Yes, you technically need to report ALL gambling winnings as income, even your $270. The threshold for casinos to issue a W-2G is $1,200+ for most table games, but that's just when THEY have to report it - you still owe taxes on smaller amounts. For your situation, report it as "Other Income" on Schedule 1 of Form 1040. The tricky part is you can deduct gambling losses against winnings IF you itemize deductions (not just take the standard deduction). So if you lost money gambling elsewhere during the year, keep those records! Honestly, for $270 the practical risk is low, but it's better to be safe than sorry. Plus once you start reporting gambling income properly, you'll be prepared if you ever hit bigger winnings in the future. Just make sure to keep better records going forward - date, location, amount won/lost, type of game. Your phone camera is your friend for documenting everything!

Just wondering - does having a SSN from your internships change anything about how you fill out the W8-BEN? I got a social when I worked in the US last summer.

Just to add one more perspective here - don't stress too much about the W8-BEN form. It's actually pretty straightforward once you understand what it's for. The key thing to remember is that this form is specifically about the interest income your bank account generates, not your employment income. Since you're Canadian, you'll definitely benefit from the tax treaty. The US-Canada treaty eliminates withholding on bank interest entirely (0% instead of 30%), so filling out this form will actually save you money on any interest you earn. One thing I'd suggest is to keep a copy of your completed W8-BEN for your records. When you do eventually become a US tax resident (which sounds like it'll happen soon with your full-time move), you'll need to notify your bank and switch to providing them with a W-9 form instead. Having documentation of when you made that transition can be helpful for tax purposes. The form itself is valid for 3 years, but your circumstances are changing, so you'll likely need to update it sooner than that. Good luck with your move!