Don't overthink this! Schedule C is definitely the right place for self-employment income, received 1099 or not. I've had missing 1099s for years from some clients and never had an issue. Just make sure the total you report matches or exceeds what was actually paid to you, and you'll be fine. The IRS mainly cares that you're not UNDER-reporting income.

Just went through this exact situation last tax season! You're absolutely doing the right thing by reporting the income on Schedule C regardless of the missing 1099-NEC. One thing I'd add that helped me - consider sending one final certified letter to the company requesting the 1099, keeping the receipt. This creates an official paper trail showing you made every reasonable effort to obtain proper documentation. Even if they don't respond, you'll have proof for your records. Also, make sure to separate the $68,000 in actual income from the $350 in reimbursements when reporting. The reimbursements shouldn't be included as income since they were just covering your expenses. Only report the true payment for services as self-employment income on Schedule C. The IRS matching system is pretty forgiving when you report MORE than what's on file rather than less. Even if that 1099 shows up later, you're already covered since you reported everything accurately.

Not sure if this helps, but I bought a patent last year and my tax guy told me the key thing is whether you aquired any "goodwill" along with it. Since my patent was for a completely different industry than my business operates in, it was clearly just an asset purchase and not part of aquiring any business operations. I was able to amortize it over its useful life (10 yrs in my case) instead of the 15-year 197 schedule.

Based on everything discussed here, it really sounds like your patent purchase wouldn't qualify as a Section 197 intangible. The fact that you bought it as part of a liquidation sale with no transfer of business operations, goodwill, or customer relationships is key. One thing I'd add is to make sure you have proper documentation of the patent's remaining useful life for your amortization calculation. Since you mentioned it has 12 years left, you'll want to support that with the original patent filing date and term. The IRS sometimes challenges useful life determinations, so having the USPTO records showing the exact expiration date will be helpful. Also, since you paid $87,000 for the patent "along with some other property," make sure you properly allocate the purchase price between the patent and the other assets. You can only amortize the portion specifically attributable to the patent itself.

Don't forget about state taxes! Even if you understand the federal NRA rules, many states have their own withholding requirements for non-residents selling property. California was brutal with a mandatory 12.3% withholding on top of the federal FIRPTA withholding when I sold my San Diego property. Arizona has their own withholding for non-residents too, I think it's around 2-4% depending on the sale price. Massachusetts might have something similar for your Boston property.

This is such a helpful thread! I'm in a similar situation - moving back to the UK next year and have been stressing about the tax implications of selling my Denver condo. One thing I wanted to add that might help others: if you're planning to maintain any US ties (like keeping US bank accounts or investment accounts), make sure you understand how that might affect your NRA status determination. I learned from my tax advisor that the IRS looks at the totality of your connections to determine tax residency, not just the day count. Also, regarding the substantial presence test - don't forget that days when you're in the US for medical treatment or as a student can be excluded from the count in certain situations. There are some nuances that might help if you're borderline on the 31-day/183-day thresholds. The state withholding point is crucial too. Colorado has its own withholding requirements, and I discovered that some states don't have reciprocal agreements with certain countries' tax treaties, so you might get federal relief but still face state-level complications. Thanks everyone for sharing your experiences - this community is invaluable for navigating these complex situations!

Has anyone here actually calculated what the penalty would be for a missed Q4 payment? I'm trying to figure out if it's worth the hassle of making a separate payment now vs just handling it when I file in April. If I owe roughly $2,000 for Q4, how bad would the penalty be?

For the IRS website issue, you're absolutely right - since we're in 2025 now, the estimated tax payment option defaults to the current year. The workaround is to use "Make a Payment" and select "Apply Payment to Account" or "Amount Owed" instead of the estimated tax option. When you get to the payment screen, you can specify tax year 2024. Regarding the 1040-ES form - your buddy is partially right. You don't need to mail the form to the IRS, but you should still use it to calculate the correct payment amount rather than just guessing based on tax brackets. The form accounts for your specific situation, deductions, and credits. It's worth the 20 minutes to fill out, especially as a new self-employed person. Don't wait until you file your return. The underpayment penalty starts accruing from the original due date (January 16, 2025 for Q4 2024), not when you file. Even if the penalty isn't huge, making the payment now shows good faith and stops the daily interest charges. Plus, you'll have one less thing to worry about when tax season gets hectic. Welcome to self-employment! The estimated tax system takes some getting used to, but you'll get the hang of it.

Quick question - what tax software are you all using to handle this kind of situation? I'm trying to include my husband's 1099-MISC on my Schedule C and TurboTax is giving me a hard time about it since the SSNs don't match.

I went through almost the exact same situation last year with my consulting business! The key thing I learned is that the IRS cares about the substance of the transaction, not just whose name is on the form. Since your 1099-MISCs from both you and your wife are directly related to your business activities in the travel rewards space, they should absolutely be reported on your Schedule C. For your wife's 1099s specifically, the fact that she helps with administrative tasks and content creation makes this pretty straightforward. That's legitimate business involvement. I'd suggest keeping a simple log of her contributions - even just a monthly summary of tasks performed. This way if you're ever questioned, you can demonstrate that her income wasn't just a paper transaction but reflects actual business participation. One thing to watch out for: make sure you're consistent year over year. If you start including her 1099s on your Schedule C, keep doing it as long as she remains involved in the business. The IRS doesn't like seeing income bounce back and forth between spouses without clear business justification. This approach also maximizes your SEP-IRA contribution limits since you're capturing all legitimate business income. Just make sure your record-keeping is solid!