Don't overlook state tax implications in whatever you decide! Some states don't recognize S corps the same way the federal government does, and others have additional fees or taxes for different entity types. California, for example, has an $800 minimum franchise tax for LLCs and S-Corps alike. If you tell us what state you're in, you might get more specific advice. The 5-year waiting period is definitely a federal rule, but your best alternative structure might depend partly on state considerations.

This is a tough situation, but you're not completely out of options. The 5-year waiting period is indeed strict, but I've seen a few successful approaches: First, definitely document everything about your business transition from side-gig to full-time. The IRS sometimes considers substantial changes in business circumstances when evaluating private letter ruling requests. Your shift from $22k hobby income to $90k primary income could be compelling evidence. Second, consider whether your original revocation was truly "voluntary" or if you were acting on incomplete information. If you can demonstrate that you didn't fully understand the consequences or didn't receive proper professional guidance, you might have grounds for relief under Revenue Procedure 2013-30. Third, look into whether forming a new entity makes sense for legitimate business reasons beyond just tax elections. If you're adding partners, significantly changing your business model, or expanding into new markets, a new LLC might be defensible. Finally, don't forget about interim tax strategies while you work through this. You can still maximize retirement contributions, consider a solo 401(k), and potentially hire family members to shift some income and reduce self-employment taxes. I'd strongly recommend getting a consultation with a tax attorney or CPA who specializes in entity elections before making any major moves. This situation is complex enough that professional guidance is worth the investment.

Some tax offices offer a "self-preparer" package where you can use their professional software but do the work yourself. I did this last year for my extended family - paid $150 for access to professional software that let me prepare unlimited returns. Each return still had e-filing fees ($25 each in my case), but it was WAY cheaper than hiring a pro for each return. Check with local tax offices in your area - many offer this in the off-season (summer/fall) at discounted rates. They technically review the returns before filing, but it's minimal if you know what you're doing.

Have you considered setting up a shared Dropbox or Google Drive folder where everyone uploads their documents? That's what I did for my family - created a secure folder structure for each person, had them upload docs throughout the year, then I blocked off a weekend to do all the returns using FreeTaxUSA. Way more efficient than doing them one by one with each person present.

One thing nobody mentioned yet - make sure you're keeping the receipts for concert tickets separate from other entertainment expenses. The IRS looks closely at entertainment deductions and they're tricky for content creators. For your concert tickets, you should document: 1. Date and venue 2. What content you produced from it (link to the review) 3. How it directly relates to your business I learned this the hard way when I got audited for my travel blog. They questioned every meal and event ticket until I could prove it was directly tied to content I published.

Great advice from everyone here! I'm actually a CPA and wanted to add a few important points that might help Diego and others in similar situations. First, since you're making $2,800/month consistently, you definitely need to make quarterly estimated tax payments. The general rule is if you expect to owe $1,000 or more in taxes, you need to pay quarterly. Calculate 25-30% of your net profit and pay that quarterly to avoid underpayment penalties. For the home office deduction, be careful - it needs to be a space used EXCLUSIVELY for business. If you edit in your living room sometimes, that doesn't qualify. But if you have a dedicated room or corner that's only for filming/editing, you can deduct that percentage of your rent, utilities, etc. Also, consider setting up an LLC or S-Corp election once your income grows more. Right now you're paying both sides of Social Security/Medicare tax (15.3% total), but there are legitimate ways to reduce some of that burden as your business grows. Keep meticulous records of everything - the IRS loves to audit content creators because the line between business and personal expenses can be blurry. Document the business purpose for every expense, especially entertainment-related ones like concert tickets.

has anyone actually had an audit after filing as a resident alien with treaty benefits? im nervous about claiming the treaty exemption and then getting flagged for an audit. is there anything specific i should document just in case?

I went through this exact same situation two years ago and it was incredibly stressful! One thing that really helped me was keeping detailed records of everything - not just for potential audits, but to make sure I was filing correctly. Since you mentioned you're in your 6th year on F-1, you're definitely correct about being a resident alien. Just make sure you have documentation showing your entry dates and status changes. I kept copies of all my I-94 records, passport stamps, and previous tax returns. For the 1042-S treaty benefits, the key is making sure you report the income AND claim the exemption properly. Don't try to hide the income - that's what gets people in trouble. Report it all transparently and let the treaty exemption do its job. One last tip: if you're still nervous about getting it right, consider having a tax professional review your return before filing, especially for your first year as a resident alien. It's a small cost for big peace of mind!

There's one thing nobody's mentioned yet that could be significant. If you DO amend as married filing jointly, be aware that both partners become jointly liable for the entire tax amount. This means if there are any issues with either person's reporting, both could be on the hook. Given the income disparity ($25-40k vs $470-950k), you might want to consider whether married filing separately might actually be better in some years than joint filing. Sometimes with very disparate incomes, the tax savings of joint filing aren't as large as you might expect. Also, think about whether you're planning to get formally married in the future. If you establish common law marriage for tax purposes now, you'd technically need a formal divorce if you ever split up, even without having had a wedding ceremony.

This is a fascinating case study in tax strategy! As someone who's dealt with complex filing situations, I'd strongly recommend getting professional help before proceeding, but your logic seems sound. One thing to consider: with your income levels, you'll want to run the numbers carefully for each year. Sometimes when one spouse has very high income and the other has low income, married filing jointly provides substantial savings due to income averaging effects, but other years it might not be as beneficial as expected due to phase-outs of deductions and credits. Also, keep in mind that amending returns of this magnitude will likely trigger enhanced scrutiny from the IRS. They'll want bulletproof documentation not just of your common law marriage status, but also of when exactly you became common law married. The July 2018 date when you moved to SC and merged finances will be critical - you'll need to show clear evidence that your relationship status changed at that specific time. Document everything: bank account opening dates, when you were added to health insurance, property records, any legal documents from that timeframe. The IRS will be looking for consistency in your story and timeline. Given the potential six-figure recovery, investing in quality legal and tax professional advice upfront could save you significant headaches later. Good luck!