What app do you use to track your travel days? I've been using a spreadsheet but it's getting messy, especially with some quick weekend trips back to the US to visit family.

I use an app called "Travel Days Tracker" - it lets you log entries/exits by country and calculates your total days for tax purposes. Some people also use the Stride Tax app which has a location tracking feature that can automatically log when you cross borders. The spreadsheet works too, but I found having the app on my phone made it easier to log immediately when crossing borders. Whatever system you use, just be consistent. The IRS can request proof of your physical presence, and border crossing records can sometimes be incomplete.

This is a really good point. New York is just as bad as California. I moved to Toronto but kept an apartment in NYC that I use occasionally. NY claimed I was still a full-year resident even though I was physically in NY less than 90 days that year.

Thanks for the info about TaxSlayer and IRS Direct Pay! I was wondering about making the payments online instead of mailing them. Does the Direct Pay system give you a confirmation that you can save for your records?

Yes, the IRS Direct Pay system provides a confirmation number immediately after your payment processes. You can print this confirmation page or save it as a PDF. I recommend doing both and keeping a folder (digital or physical) for each tax year with all your payment confirmations. They also send a confirmation email if you provide your email address during the payment process. I personally save these emails in a dedicated tax folder in my email account for easy reference later.

This is such an important point. I had the same thing happen in New York. Paid all my federal estimated taxes but completely forgot about state requirements. Ended up with almost $200 in penalties even though my actual state tax bill wasn't that high.

1 I've heard about the S-Corp option but wasn't sure if it was worth the extra paperwork and compliance requirements. What income level do you think makes the S-Corp election worthwhile? And did you need to hire a specialized accountant to handle it?

22 Most tax professionals suggest considering S-Corp election when your business profit exceeds about $40,000-$50,000 annually. That's typically where the self-employment tax savings outweigh the additional costs of compliance. I did hire a specialized accountant because the S-Corp has more filing requirements including an annual 1120S corporate return. The costs run me about $1,200 annually for tax preparation, but I save around $4,000 in self-employment taxes, so it's definitely worth it. You'll also need to run regular payroll and maintain more formal business documentation, but the tax savings can be significant once your business is consistently profitable.

11 I used TurboTax Self-Employed last year for my single-member LLC with both 1099s and W-2 (I pay myself). It worked well and walked me through reporting the 1099 income on Schedule C, entering business expenses (including my salary to myself), and then separately entering my W-2. Just make sure you enter your salary as a wage expense on Schedule C - this is critical to avoid double taxation.

7 That's a really good point. I did move about 8 months ago but stayed with the same employer. How would I go about checking if they have me in the right district?

5 You should be able to check your pay stub to see which school district they have you listed under. Look for an abbreviation or code that indicates your tax district. Then compare that with the school district that's trying to collect from you. If they don't match, that's your problem right there. You can also ask your HR or payroll department directly what school district they have on file for you. If there's a mismatch, you might have grounds to dispute the collection fees since the error wasn't your fault.

7 Well that explains why nobody told me about this when I started my job! So for future reference, how do I figure out what my school tax obligations are so this doesn't happen again? I definitely don't want another surprise bill.

Is there a way to confirm that the IRS actually received your payment if you mail it? I'm always worried it will get lost in the mail and then I'll get hit with penalties even though I sent it on time.

Yes, there are a few ways to confirm the IRS received your payment. The most reliable is to send it via USPS Certified Mail with Return Receipt requested. This gives you proof of mailing and delivery. You can also check your tax account information online through the IRS website after a few weeks to see if the payment has been applied. If you included your phone number on your check, sometimes the IRS can locate your payment status if you call and ask about it, though that can take some time on the phone.

Yes!!! This happens to me every year and it's maddening. I've started taking screenshots of everything on the IRS website just so I can prove what they told me if there's ever an issue. The worst is when they update info mid tax season without any clear notification.