I think everyone's missing a key point here - if you believe you were owed a refund for 2017, you should still file even if you can't get the money back! Why? Because it establishes a record of your income, which can be important for things like Social Security credits, loan applications, etc. Also, sometimes old returns affect newer ones. I had a carry-forward loss from an unfiled return that I needed for my current taxes. Filing the old return (even beyond the refund statute) let me properly document that loss.

This is such valuable information! I'm dealing with a similar situation with multiple unfiled returns from 2016-2019. One thing I learned from my tax preparer is that you should also check if you had any federal tax withholdings or estimated tax payments for those years. Even if you can't get a refund anymore, those payments can sometimes be applied to current tax liabilities or future years. Also, for anyone worried about the complexity of filing old returns, the IRS still accepts the tax forms from those years. You don't have to use current year forms - you can download the 2017 Form 1040 and instructions from the IRS website archives. This makes it much easier since the tax laws and forms were different back then. The peace of mind from getting these filed is worth it, even without the refund potential. No more worrying about that unfiled return hanging over your head!

My buddy got audited last year because of sports betting. He won around $4.5k total but the IRS notification made it look like he won $22k because it didn't account for his losses! The sportsbooks report your WINS to the IRS but don't report your LOSSES. So you might get a letter saying you underreported income even if you properly reported your net winnings. Keep ALL your records, especially if you're using multiple betting platforms. The $600 is just the beginning of the headache lol.

This is exactly the kind of situation that trips up new sports bettors! The $600 threshold is just when the platform has to report your winnings to the IRS - it doesn't mean they start withholding taxes automatically. You'll still be responsible for paying taxes on your net gambling income when you file. Since you're planning to stay under $6k total, you probably won't have withholding unless you hit a single large win (usually $5k+). My advice: start tracking everything now in a simple spreadsheet - date, platform, bet amount, win/loss amount. Download your betting history from each app monthly and save it. When tax time comes, you'll report your total winnings as income, and if you itemize deductions, you can deduct losses up to your winnings amount. The key thing people miss is that ALL gambling income is taxable from dollar one, not just after $600. That threshold is purely about reporting requirements, not tax liability. Keep good records and you'll be fine!

One thing I haven't seen mentioned is how the tax treaties between the US and Canada might impact your situation. As a Canadian citizen who's a US tax resident, you might be eligible for certain protections under the US-Canada tax treaty. However, tax treaties generally don't help much with offshore structures in places like the Cayman Islands. In fact, these structures often trigger anti-avoidance provisions in tax laws. My biggest concern would be that this arrangement could potentially be viewed as a tax avoidance scheme by the IRS, especially given the lack of substantial business operations in the offshore jurisdiction. The IRS has become extremely aggressive in pursuing offshore accounts in recent years.

I want to emphasize something that hasn't been fully addressed - the potential criminal penalties for willful failure to report foreign accounts. As someone who went through an offshore voluntary disclosure program, I can tell you the stakes are much higher than just paying additional taxes. The willful failure to file FBAR can result in penalties of up to 50% of the account balance PER YEAR, and in extreme cases, criminal prosecution. Given that you're talking about potentially substantial trading profits, these penalties could be devastating. Also, consider that the IRS has extensive data sharing agreements with financial institutions worldwide. Interactive Brokers, for example, reports account information to the IRS under FATCA requirements, regardless of where your account is domiciled. The idea that offshore accounts provide privacy from the US tax authorities is largely a myth in 2025. My strong recommendation would be to consult with both a US tax attorney specializing in international taxation AND a Canadian tax professional familiar with US treaty provisions before moving forward. The cost of proper planning upfront is minimal compared to the potential penalties and legal fees if this goes wrong.

Has anyone used both and can compare costs? I'm paying about $350 at H&R Block for a return with W-2, 1099 income, and some investments.

I made a similar switch two years ago and it was absolutely worth it. I was paying around $280 at H&R Block for my return with W-2, side business income, and some rental property. My EA charges $550, but the first year alone they found $4,200 in deductions I'd been missing - mostly around business use of home, equipment depreciation, and some rental property expenses that H&R Block never asked about. The biggest difference is the relationship aspect. My EA knows my situation and actively reaches out during the year with suggestions. For example, they called me in November to remind me about maximizing retirement contributions and suggested some year-end business purchases that would reduce my tax burden. That kind of proactive planning is something you'll never get from a seasonal tax chain. One tip: when interviewing EAs, ask specifically about their experience with your type of business and situation. Not all EAs are created equal either, but their baseline knowledge requirements are much higher than typical H&R Block preparers.

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.