I actually tried that first! We used Workday, but my login stopped working shortly after I left the company. I called about getting it reactivated but that just led me back to the same HR department that never answers. Frustrating because I know the W-2 is probably sitting right there in the system.

That's unfortunately pretty common - companies often disable access but don't communicate how former employees should get their tax documents. One thing you could try is reaching out to your former manager or even colleagues still at the company. Sometimes they can put internal pressure on HR that gets better results than calling from the outside. If that doesn't work, a former coworker might be able to tell you who specifically in HR handles tax documents, so you could email them directly instead of calling the general HR line. Large companies often have dedicated tax specialists who are separate from the regular HR team.

This actually worked for me last year! I filed a complaint with my state labor board and they contacted my former employer. Got my W-2 within a week after months of trying on my own.

What about the tax debt situation? Would an accountant help navigate that better than tax software?

For the tax debt situation specifically, an accountant can provide strategic advice, but they don't have any special access to the IRS. They'd likely advise you to contact the IRS directly to set up a payment plan or explore settlement options. A tax professional might be able to help determine if any of the debt can be addressed through penalty abatement requests or other relief programs. They can also advise on whether filing jointly or separately makes more sense given the outstanding debt. But for actually resolving the debt, you'll still need to work directly with the IRS one way or another.

The marriage penalty isn't as bad as it used to be after the 2017 tax changes, but it can still hit high earners. At their income level (over $400k combined), they could definitely face some penalty. I'd suggest looking at the actual tax brackets for 2024 and calculating both ways. Don't just assume joint is better!

Did you end up owing a lot more? I'm worried about making mistakes too. Did the IRS charge you penalties or just the additional tax?

Nope, unfortunately dual-status returns still can't be e-filed. I tried with both TurboTax and H&R Block last year, and both required paper filing. It's one of those weird IRS limitations that they haven't updated yet. Make sure you send it certified mail so you have proof of delivery!

I didn't even think about quarterly taxes! We haven't been paying anything throughout the year. Is it too late to fix this for last year? And how do we figure out how much to pay each quarter going forward?

It's too late to fix last year's quarterly payments now, but you can avoid penalties going forward by starting them this year. For most resellers, you need to pay estimated taxes if you expect to owe $1,000+ at tax time. For calculating the amount, you can either pay 100% of last year's tax liability divided into four payments (the "safe harbor" method), or 90% of what you expect to owe this year. I personally set aside 30% of my net profit each month and make payments on the quarterly due dates (April 15, June 15, September 15, and January 15). There's a form called 1040-ES that helps with calculations, or your tax software should have an estimated tax calculator. Start now and you'll avoid the shock next tax season!

And sales tax! If you're selling online, the marketplace might collect it for you (like eBay or Amazon) but if you sell directly you might need to collect and remit sales tax depending on your state and sales volume. That tripped me up my first year.

Is this something I could do myself or would I need my CPA to handle it? And do you know how long the process typically takes? I'm worried about interest continuing to build while I wait for a decision.

You can certainly do it yourself using the IRS's Form 656 Booklet which includes instructions, but having your CPA help might increase your chances of success since they understand what the IRS is looking for in terms of documentation and financial hardship proof. The process typically takes 6-12 months for the IRS to evaluate and make a decision. Interest and penalties do continue to accrue during this time, which is a downside. However, if you're approved, those additional amounts would be included in the settlement. If you're rejected, you'd still have the option to set up a payment plan for the full amount. Many people start with a payment plan and then apply for an Offer in Compromise if they realize they truly can't manage the payments.

Don't forget about the Qualified Business Income deduction (Section 199A)! For most freelancers, you can deduct up to 20% of your net business income. Saved me thousands last year.