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...

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.

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.

Yes, thankfully my parents are super organized with this stuff. They have every receipt, invoice, and payment confirmation from the treatment center. They even have records of the insurance claims that were denied (which is why they had to pay out of pocket). I guess the bigger question is still whether anyone can actually claim these expenses given that I'm not a dependent. Sounds like I need to look more into that "qualifying relative" test that others mentioned.

That's great that your parents kept everything. Those records will be essential if they end up being able to claim the expenses. Definitely look into the qualifying relative test. The main things they'll need to prove are: 1) that they provided more than half your support for the year, 2) that your gross income was below the threshold (around $4,500 for 2025), 3) that you lived with them all year (though there are exceptions for temporary absences including rehab), and 4) that you're related to them. If you meet all those tests, they might be able to claim both you as a dependent and the medical expenses.

This is super important! I learned this the hard way last year. Had about $8k in medical expenses but couldn't deduct a penny because my AGI was too high and the standard deduction was better anyway. Such a disappointment after saving all those receipts.

But wouldn't waiting to submit the 433-A just delay the whole process more? My revenue officer keeps pressuring me to submit mine ASAP and I'm in a similar situation with wanting to consolidate vehicles.

If your revenue officer is already involved and pressuring you for the 433-A, communication becomes key. I'd recommend being upfront with them about your vehicle plans before making any changes. Explain that you're planning to consolidate vehicles to reduce overall expenses and improve reliability, not to hide assets. In my experience, most ROs appreciate transparency and would rather you be honest about upcoming changes than submit information that will be immediately outdated. You could even ask if they prefer you to submit the 433-A with current information and an addendum explaining the planned vehicle changes, or if they'd prefer you complete the transactions first. This proactive approach usually works better than trying to time things without their knowledge.

Yes, I actually did this successfully. The key was showing that the monthly expenses for the 2 newer vehicles were actually LOWER than maintaining the 4 older ones (repair costs, insurance, etc). I provided 2 years of maintenance receipts for the old cars to prove they were money pits.