I just want to add that the standard deduction vs. itemizing decision should look at your TOTAL tax picture, not just Form 8960. Sometimes it's actually better to itemize even if it's slightly less than the standard deduction because of the impact on other forms like 8960. Have you run the numbers both ways to see which gives you the lowest overall tax?

Great point about running the numbers both ways! I actually did a quick calculation after reading your comment and you're absolutely right - even though itemizing would give me about $2,100 less in deductions compared to the standard deduction, the ability to use my investment interest expense on Form 8960 would save me roughly $450 in NIIT. So net effect: I'd pay about $500 more in regular income tax by itemizing, but save $450 in NIIT, making the total difference only about $50. Given how close it is, I might actually itemize just to have those legitimate expenses recognized somewhere on my return. This is exactly why tax planning can be so tricky - you really do need to look at the whole picture, not just individual forms. Thanks for the perspective!

Has anyone dealt with rental income specifically across borders? I'm wondering about vacation rental platform payments (like Airbnb) - does it matter if the payments go to a US bank account vs Mexican account? Does that change where the income is considered sourced from?

This is such a helpful thread! I'm dealing with something similar for my sister who just got her Mexican permanent residency but still works remotely for a US company. One thing I learned from our tax attorney is that the timing of when your mom establishes her tax residency status in Mexico matters a lot. If she files the declaration for US primary tax residence early in the tax year, it can help avoid complications later. Also, since she's starting the vacation rental next year, now would be a perfect time to set up proper record-keeping systems for both countries. The Mexican tax authority is getting much more sophisticated about cross-referencing rental platform data (Airbnb, VRBO, etc.) with tax filings. Having clean books from day one will save headaches later. For the rental property specifically, make sure she understands the depreciation rules in both countries - they're calculated differently and this can affect her overall tax strategy significantly.

Don't forget that any business expenses you had during those contractor months might be deductible on your Schedule C! This includes things like mileage if you drove for work, a portion of your phone bill if you used it for work, home office deduction if you worked from home, etc.

One thing to keep in mind is that when you file your 2025 taxes, you'll likely need to make quarterly estimated tax payments for 2025 if you expect to owe $1,000 or more in taxes. Since you now have both W-2 income and potential future contractor income, it's worth calculating this early to avoid underpayment penalties. Also, make sure your employer provides you with both a 1099-NEC for those contractor months AND a W-2 for your employee months. Some employers try to just issue a W-2 for the whole year, but that's incorrect - the contractor income needs to be reported separately on the 1099-NEC. If your employer pushes back on issuing both forms, you can point them to IRS guidelines that clearly state the income must be reported according to how you were classified when you earned it, not your status at year-end.

Has anyone else just switched to e-filing their extensions? After having a paper extension get lost a few years ago (and paying penalties because of it), I've gone completely digital. Most tax software lets you e-file the extension for free, even if you end up filing your actual return on paper later.

Great question! I had the same confusion when I first filed an extension by mail. You're absolutely correct - the address you listed is complete and proper for mailing Form 4868 without payment via USPS. The reason there's no building number is that USPS has special routing agreements with federal agencies. When you include payment or use private carriers like FedEx/UPS, they need the specific building number because they don't have those same routing systems in place. One thing I'd add - if you're concerned about proof of delivery, consider sending it certified mail with return receipt. It only costs a few extra dollars but gives you peace of mind that it arrived on time. The postmark date is what matters for meeting the deadline, so as long as you mail it by April 15th (or whatever the current deadline is), you're covered even if it takes a few days to reach the IRS. Good luck with your extension!

Just want to add a quick warning - while you're sorting this out, make sure you respond to any IRS notices within the timeframes they specify, even if it's just to tell them you're disputing the issue. If you ignore notices completely, it can lead to escalation regardless of whether you're in the right or not. I learned this the hard way when I had a similar payment issue. I knew I had paid and figured it would sort itself out, so I ignored a couple of follow-up notices. Big mistake! That led to them sending me to collections even though I had proof of payment. Once you're in collections, everything gets more complicated and stressful.

I went through almost the exact same situation with payusatax.com last year! The key thing that finally worked for me was being extremely persistent with their customer service. Here's what I did: 1. Called them every single day at 8 AM sharp when they opened - I found that's when you're most likely to get through to an actual person rather than being stuck in their phone tree. 2. When I finally got someone on the phone, I immediately asked to speak to a supervisor about a "missing EFT reference number for IRS payment dispute." Using that specific language seemed to get me transferred to someone who actually knew what they were talking about. 3. I had my confirmation number, payment date, and credit card statement ready before I called. They were able to look up my payment in their system and provide the EFT reference number on the spot. The whole process took about two weeks of daily calls, but once I got the EFT number, I was able to provide it to the IRS and everything was resolved within a few days. Don't give up - the payment is definitely in their system somewhere, you just need to find the right person who can access it. Also, make sure you're calling payusatax directly and not going through any third-party sites that might look similar. Their real customer service number should be on your original payment confirmation email.