Just want to add another option to consider: Delaware Statutory Trusts (DSTs) through a 1031 exchange. First, you'd need to convert your stock proceeds into investment real estate (even a small property would work), then you could 1031 exchange into DST interests. DSTs are passive investments in institutional-quality real estate. You get: - Tax deferral through the 1031 exchange - Professional management (solving your time constraint issue) - Regular income from the properties - Potential appreciation The catch is that first step - you need to buy real estate before you can 1031 into a DST. Given your timeline with the acquisition, this might be challenging, but worth exploring.

For someone in your situation with $1.8M in forced capital gains, I'd strongly recommend working with a tax professional who specializes in large capital gains events - this isn't the time for DIY tax planning given the amounts involved. A few additional considerations beyond what's already been mentioned: **Installment Sales**: Even though it's an acquisition, check if the buyer might structure part of the payment as deferred consideration or earnouts. This could spread the gain over multiple years. **Net Investment Income Tax**: Don't forget about the 3.8% NIIT on top of capital gains rates for high earners. This affects your total tax calculation. **State Tax Planning**: Depending on your state, you might benefit from establishing residency in a no-capital-gains-tax state before the sale if feasible and legitimate. **Bunching Deductions**: Since you'll have a high-income year, consider bunching charitable deductions, state/local taxes (up to the $10K limit), and other itemized deductions into this tax year. The QOZ route seems most promising for your situation, but due diligence on fund quality is absolutely critical. Look for funds with experienced real estate developers, clear business plans, and regular investor reporting. Avoid anything that feels like a pure tax play without underlying investment merit. Given the 180-day deadline for QOZ investments after your stock sale, start your research now so you're ready to move quickly once the acquisition closes.

One thing nobody's mentioned yet is state tax considerations. I'm a Brazilian with a Wyoming LLC and discovered that even though I don't have federal tax filing requirements as a non-resident alien (beyond the Form 5472 already mentioned), some states might still require filing. Wyoming is great because there's no state income tax, but if you formed your LLC in a state with income tax, you might have state filing requirements even without US-source income.

This thread has been incredibly helpful! I'm in a similar situation as a Canadian citizen with a Delaware LLC (mistake on my part - should have gone with Wyoming!). Just wanted to confirm something based on what I'm reading here: if I'm providing digital marketing services to US clients entirely from my home office in Toronto, I would use W-8BEN-E and NOT claim any effectively connected income, correct? My services are performed 100% remotely with no US physical presence. Also, the Form 5472 requirement is news to me - I've been operating for 8 months and had no idea about this filing obligation. Is there any relief for reasonable cause if you genuinely didn't know about the requirement? That $25k penalty is absolutely terrifying for a small business owner. Thanks to everyone who shared their experiences - this is exactly the kind of real-world guidance that's impossible to find in IRS publications!

Might be a dumb question but does taking online classes from your home country count as being "present in the US" for the substantial presence test? I was stuck in my home country during part of 2022 due to COVID but still enrolled in US university online.

Just wanted to add some clarity about the 5-year exempt period for F-1 students since there seems to be some confusion in the thread. The 5 calendar years start counting from the first year you were present in the US on F-1 status, regardless of how many days you were actually here. So for the original poster who first entered in 2019, your exempt years would be 2019, 2020, 2021, 2022, and 2023. This means 2024 would be your first year where days count toward the substantial presence test. However, since you were only present for about 240 days in 2024 (and this is your first countable year), you likely don't meet the substantial presence test yet and would still file as a non-resident alien using Form 1040NR. One important thing to remember: even as a non-resident alien, your US-source income (like your on-campus job) is still fully taxable. You'll report this on Form 1040NR, and depending on your home country's tax treaty with the US, you might qualify for certain exemptions or reduced tax rates.

Something nobody's mentioned yet - having a business license can actually help support the legitimacy of your business if you're ever questioned by the IRS. While not required for deductions, it's additional evidence that you're running a genuine business rather than claiming a hobby as a business to deduct expenses. Also, your state and local requirements matter a lot. In my city, operating without a required business license could result in fines that far outweigh any tax benefits. I'd recommend checking your local requirements regardless of the tax implications.

One thing to remember that no one mentioned - if u don't have a business license and ur supposed to in ur city, the IRS might share info with local authorities which could lead to fines. Happened to my friend! Also don't forget about self-employment taxes (15.3%) on top of regular income tax. Those hit hard when ur not expecting them!

Just a tip from someone who used to work at the IRS - if your amended return included any items related to the Recovery Rebate Credit or any pandemic-related tax credits, those are facing the WORST delays. The IRS implemented special review procedures for those items, and many got stuck in manual review queues. If your amendment is related to anything like that, make sure to mention it specifically when you finally get through to someone. There are special teams handling those specific issues, and sometimes returns get stuck in the general queue when they should be routed to a specialized unit.

I completely understand your frustration - 130 weeks is absolutely unacceptable for an amended return! I went through something similar with my 2020 amended return that took 18 months to process. Based on what others have shared here, I'd strongly recommend trying multiple approaches at once: 1. Contact your congressional representative's office for a congressional inquiry - this seems to be one of the most effective methods based on the success stories here. 2. Call the Taxpayer Advocate Service at 1-877-777-4778. After 2.5 years, you definitely qualify for their assistance due to excessive processing delays. 3. If you can't get through to the IRS directly, consider using a service like Claimyr to help you actually reach a human agent who can look up your specific case. The key thing is that your return is likely stuck somewhere in the system rather than actually being "processed." You need someone with internal access to identify exactly where it's sitting and get it moved to the right department. Don't give up - $1,890 is a significant amount of money and you deserve to get what you're owed! Keep us updated on what works for you. Your situation might help others who are dealing with similar delays.