Which tax software would be better for a sole proprietor LLC? I've heard mixed things about both TurboTax and H&R Block. Anyone try both?

I'm in a very similar situation - made about $18k from my freelance marketing business this year and also totally neglected the quarterly payments (oops!). After reading through all these responses, I'm definitely going with TurboTax Self-Employed. One thing I'd add that hasn't been mentioned - if you have any business-related subscriptions or software you pay for monthly (like Adobe Creative Suite, project management tools, etc.), make sure you have those receipts ready. Those add up quickly and are fully deductible. I went through my credit card statements and found almost $800 in software subscriptions I had forgotten about. Also, don't beat yourself up about the quarterly payments thing - apparently it's super common for first-year freelancers. The penalty really isn't that scary at our income levels. Just get it done and set up those quarterly payments for next year!

Something that hasn't been mentioned yet - even if you qualify as a non-resident alien and get your FICA taxes refunded, you still need to file a tax return! You'll need to file Form 1040-NR (Non-resident Alien Income Tax Return) for the income you earned while working in the US. Also, if you don't mind sharing, which state were you working in? Some states have different rules about residency and taxation that might affect your situation beyond just the federal considerations.

Massachusetts follows federal guidelines for most residency determinations, so you should be fine there. The state generally recognizes the same exempt individual status for J-1 visa holders that the federal government does. One tip for your FICA refund - if your employer is being uncooperative about providing the required documentation, you can also request your wage and tax statement directly from the Social Security Administration using Form SSA-7050. This shows all wages reported and FICA taxes paid, which can serve as backup documentation for your Form 843 filing. Also, keep detailed records of your entry/exit dates from the US. The CBP I-94 website only keeps records for a limited time, so print or save screenshots of your travel history now while it's still available. You'll want this documentation both for your FICA refund and to prove your substantial presence test calculations if the IRS ever questions them. Good luck with your refund - $3,300 is definitely worth pursuing!

Don't forget about the Net Investment Income Tax (NIIT) of 3.8% that kicks in for investment income when your modified adjusted gross income exceeds $200,000 for single filers. With $105k in capital gains plus your other income, you might be approaching that threshold.

Congrats on the successful trades! Here are a few additional things to consider that haven't been fully covered: 1) **Estimated Tax Safe Harbor Clarification**: Since your prior year tax was $3,100, you need to pay at least 100% of that (not 110%) to avoid penalties, as the 110% rule only applies if your prior year AGI exceeded $150,000. Your $3,000 in quarterly payments gets you very close. 2) **Form 8949 Preparation**: Start organizing your trade data now. You'll need specific details for each transaction (date acquired, date sold, proceeds, cost basis) for Form 8949. Most brokerages provide this in a downloadable format. 3) **Estimated Tax for 2025**: Don't forget that you'll likely need to make much larger quarterly payments next year if you plan to continue trading. The IRS expects you to pay based on your current year's expected income. 4) **Record Keeping**: Document everything related to these trades - confirmations, statements, any fees paid. The IRS can audit investment income, and good records are essential. Since you mentioned being overseas, also verify that your trades don't trigger any FBAR (Foreign Bank Account Report) requirements if you used foreign brokerage accounts.

One approach that's worked really well for me is using a hybrid strategy. I calculate a baseline quarterly payment using the safe harbor method (100% or 110% of last year's tax), but I make it slightly lower - maybe 80% of that amount. Then I supplement with increased W-4 withholding from my regular job later in the year once I have a clearer picture of my actual gains. This gives me the best of both worlds: I'm covered by the safe harbor rules so I won't get penalties, but I'm not massively overpaying early in the year when my trading results are still unknown. If I end up having a great year in the markets, I can always increase my payroll withholding in Q3 or Q4 to cover the difference. If the market tanks and I have losses, I'm not stuck having overpaid by huge amounts in my early quarterly payments. The key insight is that you don't have to choose just one method - you can combine estimated payments with increased withholding to create a more flexible approach that adapts to your actual trading results throughout the year.

This is such a common struggle with unpredictable investment income! I've been through this exact situation and here's what I learned: the key is understanding that the IRS safe harbor rules are designed specifically for situations like yours where income is hard to predict. The 100%/110% of prior year tax rule is actually your friend here, even if it feels like you're overpaying. Think of it as insurance against penalties - you're guaranteed to avoid underpayment penalties regardless of what happens in the markets. And if you do overpay, that money comes back to you as a refund (essentially an interest-free loan to the government, but better than paying penalties). For someone in your situation with $35k in unexpected gains, I'd recommend calculating your total 2024 tax liability and then paying 100% of that amount (or 110% if your AGI was over $150k) in equal quarterly installments for 2025. This gives you complete peace of mind while you're focusing on your trading decisions. Also consider the hybrid approach another member mentioned - you can combine quarterly payments with increased W-4 withholding from any regular job income to create more flexibility as the year progresses. The most important thing is getting started with some system rather than doing nothing and risking penalties again.

Has anyone tried doing the 1065 through Cash App Taxes (formerly Credit Karma Tax)? I use it for my personal taxes and love that it's totally free, but not sure if their business version handles LLCs well.

I've been filing my LLC's 1065 returns for the past 3 years and can definitely relate to the sticker shock from TurboTax! Here are a few more options that have worked well for me: **TaxHawk** - Usually around $70-75 for 1065 filing. Their interview process is pretty thorough and catches most common mistakes. I like that they show you exactly which forms and schedules you're generating as you go. **Drake Tax** - This one's more designed for tax pros but they do offer a consumer version. It's about $60 for partnership returns and has really robust depreciation handling if you have business equipment or vehicles. One thing I learned the hard way: make sure whatever service you pick can handle your state filing too if needed. Some of the cheaper federal options charge almost as much for state as they do for federal, which kills the savings. Also, since you mentioned your accountant retired - consider reaching out to local CPAs for quotes on just reviewing your return after you prepare it yourself. Many will do a quick review for $100-150, which gives you peace of mind without paying for full preparation. Sometimes catching one mistake saves you way more than the review fee!