Did you have to do anything special with your bank to make the Direct Pay work? My US credit card always gets flagged for fraud when I try to use it from overseas for anything government-related.

I did have to call my bank first to put a travel notice on my card and specifically mention I would be making a payment to the IRS. Even with that, my first attempt was declined and I had to verify it wasn't fraud via text message. I recommend trying the payment a few days before you need to submit it, just in case you run into issues. My backup plan was to have my parents make the payment from their account in the US if my card kept getting declined. The IRS doesn't actually require the payment to come from your personal account - it just needs to be properly attributed to your tax ID/SSN.

You're not alone in the confusion! Form 2350 is specifically for US citizens or residents who are abroad and need more time to meet either the bona fide residence test or the physical presence test to qualify for special tax treatments like the Foreign Earned Income Exclusion. Form 4868 only gives you until October 15, while Form 2350 can potentially give you more time (up to a 6-month extension, and sometimes more if needed specifically to meet those residency/presence tests). If you're trying to qualify for those expat benefits, 2350 is usually better.

Thanks for mentioning this! I just checked with my HR department and they confirmed our plan (also Fidelity) does accept IRA rollovers, but only of the pretax portion. They said they'll need a statement from my IRA custodian that clearly shows the breakdown of pretax vs. after-tax amounts. That's really helpful to know before I start the process. One question though - do you know if there's a specific form that Fidelity requires for this? My HR person wasn't sure about the exact paperwork.

For Fidelity specifically, they have a form called "Transfer/Rollover/Exchange Form" that you need to fill out. You can find it on their website or they can send it to you. Make sure you check the box that indicates it's a direct rollover from an IRA to your employer plan. Additionally, you'll need a statement or letter from your current IRA custodian that clearly breaks down the pretax and after-tax portions. Some custodians have a specific form for this, others will just generate a letter if you explain what you need.

This is super important! A buddy of mine got hit with an unexpected tax bill because he did these steps in the wrong order. The timing really matters.

What about stuff that's definitely dual-purpose? I bought a nice printer that I use maybe 70% for my business and 30% for kids' homework. Can I still deduct the whole thing or just part of it?

For dual-purpose equipment like your printer, you should only deduct the business percentage. So if it's genuinely 70% business use, you'd deduct 70% of the cost. For higher-value items like printers, computers, or tablets, it's especially important to be accurate with business-use percentages since these are more likely to be questioned in an audit. Keep a log for a few weeks showing how often you use it for business versus personal to support your percentage. Some of my clients even keep separate user profiles on their computers to help demonstrate the split use.

This is terrible advice. My friend got audited specifically over office supplies because they were deducting things without proper documentation. They ended up having to pay back taxes plus penalties. Just because YOU haven't been audited doesn't mean it doesn't happen.

That's a really helpful distinction. Do you think it's reasonable to expect both services from the same person? Or should I be looking for two separate professionals - one for planning and one for preparation?

Most comprehensive CPAs should be able to provide both services, but you may need to specifically request and possibly pay extra for the planning component. Many tax professionals offer tiered service packages - basic preparation at one price point and more comprehensive planning at a higher price. For someone in your situation with increasing income, business activities, and life changes like marriage, I'd definitely recommend finding one person who can handle both aspects. Just be clear about your expectations upfront and make sure they explicitly offer tax planning as part of their services.

Tax software is fine for simple situations but it misses a lot for complex cases. I tried this approach with my small business and rental properties and ended up getting audited because the software didn't properly handle some depreciation calculations. A good CPA is worth every penny for complicated tax situations.

You're right that it's not for everyone. I should have mentioned my situation is pretty straightforward - W2 income, mortgage, some investments. For folks with businesses, rental properties or more complex situations, a CPA probably makes more sense. I still think tax software has gotten much better at prompting for common deductions and credits though. Mine specifically asked about HDHP coverage and whether it was individual or family, then calculated the maximum HSA contribution automatically.

Thanks for breaking this down! One follow up question - does my girlfriend's income from last year affect whether I can claim her as a dependent? She made about $4,500 in 2024 but expects to make more this year.

For dependency purposes, what matters is her income in the actual tax year you're filing for. So if you're filing 2024 taxes, it's her 2024 income that counts. If she made $4,500 in 2024, that's under the threshold ($4,700), so that part of the dependency test would be met. What would affect your 2025 taxes would be her income during 2025. If she expects to make more than the threshold in 2025, then you likely wouldn't be able to claim her as a dependent when you file your 2025 taxes next year.

You can only file as Married Filing Separately if you're legally married. OP specifically said they're unmarried and living with a girlfriend, so that's not an option for them.