That's an interesting idea I hadn't thought about! He's 52, so he could do the $8,000 contribution. Would he be able to just move some of the CD money directly into a Roth or would he need to wait until the CD matures? Also, are there income limits for Roth contributions that might affect him?

He would likely need to wait until the CD matures unless he's willing to pay an early withdrawal penalty, which would probably negate some of the tax benefits. Yes, there are income limits for Roth IRA contributions. For 2025, a single filer starts to see reduced contribution limits at around $146,000 and is completely phased out at $161,000. With his $75K self-employment income plus $12K in interest, he should be well under those limits, so he'd be eligible for the full contribution.

This is super important advice! I didn't make estimated payments on some investment income last year and got hit with an underpayment penalty. It wasn't huge but still annoying to pay extra for no reason.

This is actually a really good point. I got audited last year because I had 4 years of small losses in my photography business, and the IRS questioned whether it was a legitimate business or just a hobby. Had to provide a ton of documentation showing I was actively trying to make it profitable.

Thankfully I stayed in the same state, just moved to a different city. But good point about checking state taxes for anyone who crosses state lines! Did your employer automatically split the state tax withholding correctly on your W2?

My employer did split the state withholding correctly, but they messed up the calculation slightly. They withheld at the Ohio rate for too long after I moved to Pennsylvania. I ended up owing a bit to Pennsylvania and getting a slightly larger refund from Ohio. The key is to check the withholding amounts against what you actually owed in each state based on your income during the time you lived there. If you worked remotely at all, it gets even more complicated because some states try to tax you based on where the work was performed while others go by your residence.

This is such important advice! My husband didn't notify his employer when we moved last year and they kept withholding taxes for our old city. Created a huge headache at tax time.

I did that last year - hired a cross-border tax specialist for my France/Luxembourg situation. It cost about €400 but saved me nearly €2,800 in properly claimed deductions. Make sure you find someone who specializes in BOTH countries though, not just a general "international tax expert.

That's helpful, thanks! €400 sounds reasonable for the peace of mind. Did you find them locally or use an online service? I'm having trouble finding someone who knows both Portuguese and UK tax systems.

12 This worked for me! My ex-employer was ignoring my calls about a missing 1099, but when I showed up in person they printed me a new one on the spot. Sometimes the old-school approach works best.

4 Showing up in person definitely cuts through the bureaucracy. Most HR departments are overwhelmed this time of year but they'll prioritize someone standing right in front of them. As for digital systems, that's absolutely right. Many companies use these platforms, and employees retain access even after leaving. The login credentials should still work, and you can usually download W2s from the past few years. It's worth checking your email for any registration information you might have received when you started working there.

19 The mail tampering angle might feel satisfying but it's probably not worth the hassle. My cousin went through something similar and filing the complaint just created more drama without actually solving the immediate problem. The IRS transcript route is definitely cleaner.