I've been filing from Germany for the past 4 years and have always used my local PO Box without any issues. The key thing I learned early on is to be proactive about it - I include a brief statement with my return explaining that I'm using the PO Box for reliable mail delivery while residing overseas, and I provide my physical German address as well. What really helped me was calling the IRS during my first year abroad (used a callback service since international calling was impossible) and asking them to put a note on my account about my address situation. The agent told me this is extremely common for expats and they actually prefer when people use reliable mailing addresses rather than risking missed communications. One thing to consider for Singapore specifically - I have colleagues there who mentioned that some apartment complexes have had issues with mail theft, so your PO Box idea is probably the smart move. Just make sure to keep your physical address updated with the IRS in case they ever need to verify your actual residence for any reason.

As someone who's been living in various Southeast Asian countries for the past 6 years while maintaining US tax obligations, I can definitely relate to your concerns about mail reliability in Singapore. Your PO Box approach is absolutely the right call - I've seen too many expats miss critical IRS notices because of unreliable apartment mail delivery. A few practical tips from my experience: First, definitely include that explanatory statement you mentioned. I always attach a simple note saying "PO Box used for reliable mail delivery. Physical residence address: [full street address]" right after page 2 of Form 1040. Second, consider getting a Form 8822 on file with the IRS to officially document both your PO Box and physical address - this creates a paper trail that can help if questions arise later. One thing specific to Singapore that might help: if you're working for a multinational company there, check if they offer any expat tax support services. Many of the larger firms have relationships with tax professionals who specialize in US expat filings and can provide additional peace of mind about address-related compliance issues. The IRS definitely understands that international mail can be problematic - they'd much rather you receive their communications reliably than miss them entirely due to mail delivery issues.

Has anyone used the IRS Tax Withholding Estimator on the official IRS website? I had a similar situation with extra dividend income and it helped me figure out exactly how to adjust my W-4.

Just wanted to share my experience with a similar situation last year. I had about $8k in unexpected interest income and was really worried about underpayment penalties. What worked for me was increasing my withholding through my employer rather than doing quarterly payments. I calculated roughly how much extra tax I'd owe (used the 22% bracket estimate that Melody mentioned), then divided that by my remaining paychecks and added that amount to line 4(c) on my W-4. The nice thing about this approach is that the IRS considers withholding from your paycheck as if it was paid evenly throughout the year, even if you only increase it in the last few months. So you avoid penalties even if you make the adjustment later in the year. One tip: I'd suggest being slightly conservative and withholding a bit more than your calculation, just to be safe. You'll get any overpayment back as a refund, but it's better than owing at tax time!

Has anyone used TurboTax for handling rental property depreciation? I'm wondering if the premium version can handle something like a roof replacement correctly or if I need to go to a CPA for this.

Based on what everyone's discussed here, it looks like you're dealing with a classic capital improvement situation. A $24,500 complete roof replacement definitely falls under capital improvements that need to be depreciated over 27.5 years for residential rental property. While bonus depreciation would be amazing for cash flow, residential rental property improvements like roofs generally don't qualify - they follow the same depreciation schedule as the building itself. Section 179 is also off the table for rental properties. Here's what I'd suggest: set up the depreciation over 27.5 years starting from when the roof was placed in service (likely when completed last summer). This means you'll be able to deduct roughly $890 per year ($24,500 ÷ 27.5 years) for the next 27.5 years. Not as exciting as a big first-year deduction, but it's the correct treatment under current tax law. Given the complexity and the dollar amount involved, it might be worth having a CPA review your return to make sure everything's handled correctly. The depreciation recapture rules when you eventually sell the property can get tricky too.

Something else to consider - location matters too! Some states offer state-level earned income tax credits to ITIN filers even when they're ineligible for the federal EITC. California, Colorado, Maryland, and a few others have inclusive state credits that can boost refunds for undocumented taxpayers with dependents.

This is a really comprehensive discussion! One thing I'd add is that documentation requirements can also create differences in practice. While both citizens and ITIN holders can claim dependents, citizens typically have easier access to required documents like Social Security cards for their children. For mixed-status families where some children are citizens and others aren't, the tax benefits can vary significantly per child within the same household. Citizen children with SSNs qualify for more credits than children without SSNs, even when claimed by the same parent. This creates complexity that many families don't realize until they're preparing their taxes. Also worth noting that some undocumented immigrants overpay taxes through withholding but don't file returns to claim refunds due to fear or lack of knowledge about their rights. The IRS estimates billions in unclaimed refunds each year, with a significant portion likely from immigrant communities.

I wonder if it's worth trying a different tax software? I started with TurboTax and it said I had to mail my Oregon return, but when I tried FreeTaxUSA with the exact same information, it let me e-file with no problems. Could be worth the time to input your info elsewhere if you really want to avoid mailing.

Another thing to check is whether you're filing early in the tax season. I had this exact problem with Michigan a couple years ago - filed in late January and was forced to mail my return even though my situation was straightforward. When I called the state tax department, they explained that they sometimes disable e-filing for certain forms or situations at the very beginning of tax season while they're still testing their systems. The rep suggested I wait until mid-February and try again. Sure enough, when I re-submitted the same return information a few weeks later, it went through electronically with no issues. Might be worth holding off for a couple weeks if you filed very early, especially since you mentioned this hasn't been a problem in previous years.