Thanks for this tip about Form 4852! I didn't know that was an option. Do you have to try contacting your employer first before using this form? And did you face any issues with the IRS accepting your return with the substitute form?

Yes, you should make a reasonable effort to get your W-2 from your employer first. The form asks you to describe the steps you took to obtain the missing W-2. In my case, I documented my calls to the company's HR department and the bankruptcy trustee. I didn't have any issues with the IRS accepting my return with Form 4852. Just make sure your income and withholding estimates are as accurate as possible using your last paystub. If your employer eventually sends a W-2 that differs significantly from your estimates, you might need to file an amended return, but in my experience the paystub information was very close to what would have been on the W-2.

I accidentally underestimated by about $3k last year. Got hit with the failure-to-pay penalty (0.5% per month on the unpaid amount) plus interest. For me it ended up being about $120 in penalties total. Not the end of the world but definitely avoidable if you can estimate better.

I've found that if you can show you made a "good faith effort" to estimate correctly, sometimes the IRS will waive the penalties. Document everything about why your estimate was off. In my case, I had a surprise capital gains distribution from a mutual fund that I didn't know about when filing the extension, and the IRS accepted my explanation and waived most of the penalties.

Thanks for the advice! Is the IRS calculator easy to use? We're definitely going to look into increasing our 401k contributions too.

The IRS calculator is pretty straightforward. Just have your most recent paystubs and tax return handy. It walks you step by step and gives you exact numbers to put on your W-4. Took me about 15 minutes to complete. For the 401k strategy, it made a big difference for us. If you both max out at $23,000 each (for 2025), that's $46,000 of income that moves from your highest tax bracket down to zero tax now. Plus it helps with retirement, obviously. The HSA is another great option if you have a high-deductible health plan - that's another $8,300 you can shield from taxes if you're on a family plan.

Usually MFS is worse than MFJ for most people. You lose a bunch of credits and deductions when filing separately. I'm a tax preparer and only recommend it in very specific situations like income-based student loan repayment or when one spouse has sketchy tax issues.

I hadn't even considered the HSA option! We do have a high-deductible plan through my wife's work. Do HSA contributions have the same deadline as IRA contributions where we can make them up until tax day?

Yes, HSA contributions follow the same deadline as IRA contributions! You can make contributions for the previous tax year up until the tax filing deadline (usually April 15th). Your HSA provider will give you the option to designate which tax year the contribution is for when you make it between January and April. For 2025, the contribution limit for family coverage is $8,300 (it may be adjusted for inflation), which gives you significant room to reduce your AGI. The great part about HSAs is that unlike FSAs, the money never expires, and you can invest it for the long term if you don't need it for immediate medical expenses.

Wait, really? I thought EITC was just based on AGI and number of kids. What's this about investment income? Now I'm worried because I sold some stocks this year...

Thank you for the warning. I'm definitely concerned about what else might be lurking that I don't know about. Do you think we should postpone house hunting until this is completely resolved? How long did it take your ex to get everything cleared up?

Absolutely postpone house hunting until this is 100% resolved. You don't want your dream home connected to his tax issues in any way. It took my ex almost 18 months to get everything sorted out and set up on a payment plan, and that was with hiring a tax resolution firm. Besides the immediate tax issues, consider this a pretty big red flag about financial responsibility and communication. Not filing taxes for multiple years doesn't happen by accident - it's a series of deliberate choices. Before joining finances in any way (including a mortgage), make sure you're comfortable with his approach to money and obligations.

This is good advice but some of those deductions might not be allowed. Like the IRS doesn't consider regular commuting as deductible mileage, only travel between job sites. And clothes have to be specialized for the job, not just stuff you could wear elsewhere.

That's a really smart approach I hadn't considered. I do have some procedures I've been putting off that aren't urgent. If I bundle everything together in one tax year, that might push me over the threshold where itemizing makes sense. Did you find it complicated to coordinate the timing with your providers?

It wasn't too difficult to coordinate with providers. Most medical offices are used to patients timing procedures for insurance reasons anyway, so they didn't bat an eye when I asked to schedule in January instead of December. Just make sure you're clear about your timing needs when scheduling. And keep in mind that some procedures might have wait times, so plan ahead. Also, don't let tax considerations override medical necessity - if you need something urgently, get it done regardless of the tax implications.

What qualifies someone as a dependent for medical expense purposes? My dad lives with me and I pay most of his bills, but he gets social security. Does that disqualify him?