Thanks for bringing this up! I do have about $3,000 a year from a small side gig. Should I be accounting for that directly on the W4 or should I be doing those quarterly payments you mentioned?

For $3,000 in side income, you have two options. You can include it on your W4 by adding the estimated tax amount in Step 4(a) as "other income" which will increase your withholding from your main job to cover it. Alternatively, you could make quarterly estimated payments. This is often better if your side income fluctuates a lot. The rule of thumb is if you expect to owe more than $1,000 at tax time, you should make estimated payments to avoid an underpayment penalty. For $3,000 in extra income, you're probably looking at around $500-700 in additional tax depending on your tax bracket.

This is bad advice. Blanket recommendations like "put an extra $50" don't account for specific situations. That could be way too much or too little depending on income level and other factors. The whole point of the new W4 is to be more precise.

I completely forgot about state taxes! Do I need to make quarterly payments to the state too, or is that a different process from the federal estimated payments?

Yes, many states require quarterly estimated tax payments similar to the federal system, though the due dates and calculation methods might be slightly different. Your state's department of revenue or taxation website should have forms and information specifically for estimated taxes. Some states even have lower thresholds than the federal government for when you're required to make estimated payments, so don't assume the rules are identical.

I've heard good things about FreeTaxUSA too. Much cheaper than TurboTax but still handles self-employment well. Anyone tried it?

Thanks for the insight! Do you think it would help if I reached out to individual board members instead of just the property manager? Or should I bring it up at the next board meeting?

Definitely reach out to board members directly. Property managers sometimes filter what gets to the board, and your board members might not even be aware of your request. I'd send an email to the board president specifically. Bringing it up at a board meeting is also effective. Put your request in writing beforehand asking to be added to the meeting agenda. When other owners hear about it, they'll likely want the same information, which puts pressure on the board to address it properly. Most board members are just owners like you and would want this documentation for their own taxes too.

This is what I did with my townhouse. Our HOA wouldn't provide individual breakdowns, but I found the property tax line in the annual budget and calculated my share based on square footage. I've been deducting it for years with no problems.

Is there any way to verify directly with the IRS that your 1099s were properly filed? Or do you just have to trust the service you used?

Unfortunately, the IRS doesn't have a simple verification system for confirming 1099-NEC filings. This is why getting the acknowledgment receipt with submission ID from your e-filing provider is so crucial. You can call the IRS Business & Specialty Tax Line (800-829-4933) and ask them to check if your forms were received, but be prepared for long wait times and potentially inconclusive answers. Sometimes they can confirm receipt, but they often tell you to just wait to see if you receive any non-filing notices, which isn't very helpful when you're trying to be proactive.

That's incorrect information that could cause serious problems. The threshold change to 250 (not 25) forms was actually implemented years ago, then reduced back to 10 forms for 1099-NEC specifically. For the 2024 tax year (filing in 2025), the threshold is still 10 forms, meaning OP must e-file since they have 12 forms. Filing incorrectly based on misunderstood future rule changes could result in penalties. The safest approach is to follow current requirements and use an authorized e-file provider as suggested earlier.

Wait, I've been overseas for 8 months now. Does that mean I might have qualified for that automatic extension? Do they just give it to you, or do you need to specifically request it? Also, do you know if that Foreign Earned Income thing requires you to have been overseas for a certain amount of time?

The automatic 2-month extension is given automatically to US citizens living abroad - you don't need to request it. However, it only extends the original April deadline to June, not the October extension deadline. So in your current situation, it wouldn't help unfortunately. For the Foreign Earned Income Exclusion, you typically need to meet either the Physical Presence Test (physically present in foreign countries for at least 330 days in a 12-month period) or the Bona Fide Residence Test (establish residence in a foreign country for an uninterrupted period that includes an entire tax year). Since you've been abroad 8 months, you might qualify under the Physical Presence Test depending on your specific dates. It's definitely worth looking into because it could exclude up to $120,000 of foreign earned income from US taxation.

I've sent tax docs from Japan twice now. Definitely use a courier service like DHL or FedEx rather than regular mail. They're much more reliable and give you tracking info. The IRS address you use depends on whether you're enclosing a payment - it should be listed on the IRS website under "where to file." Make sure to keep copies of EVERYTHING and proof of mailing.