Do you know any good resources to keep track of these changing tax provisions? I always seem to find out about extensions after I've already filed.

I usually check the IRS website directly in January before tax season starts. They publish updates on extended provisions. The other resource I've found helpful is following the IRS newsroom (https://www.irs.gov/newsroom) which announces major tax law changes. Tax software usually updates quickly too, but if you file early in the season, sometimes they haven't incorporated the latest extensions that Congress passes at the last minute. That's why I generally wait until at least mid-February to file if I think I might benefit from typically extended provisions like the mortgage insurance premium deduction.

Yes, PMI on a refinanced mortgage would qualify for the deduction in 2018-2019, as long as the loan was primarily for home acquisition debt (buying, building, or substantially improving your home). If you took out some cash but it was minor compared to the refinance amount, the PMI should still be deductible. The key factor is that the insurance contract needed to be issued after 2006 and the loan had to be for your primary or second home, not an investment property.

Omg thank you for mentioning this! I totally would have forgotten about the state part. Do you know if most CPAs automatically handle both the federal and state extensions when you ask them to file an extension?

Most CPAs will handle both federal and state extensions automatically if they know which state(s) you need to file in. It's part of their standard process, but it never hurts to specifically ask to make sure they're filing all necessary extensions. Always good to explicitly confirm they're handling both, especially if you have multi-state filing requirements or if you've recently moved. Different states have different rules about extensions too - some automatically grant the same extension as federal while others require their own form.

This is really good advice. I always send in a payment with my extension just to be safe, even when I think I'm getting a refund. Better to get that money back later than pay penalties!

We do own a home, so I'll make sure the mortgage interest is included. I think we've got about $8k in state taxes too. Do you know if student loan interest is still deductible if we file MFS for the IDR benefits?

Unfortunately, one of the major downsides of filing MFS is that you cannot deduct student loan interest. This is one of several tax benefits you lose when filing separately. The student loan interest deduction starts phasing out at $75,000 for single filers and $155,000 for joint filers, and is eliminated completely at $90,000 and $185,000 respectively. You should definitely make sure you're capturing the mortgage interest and state/local taxes (SALT). Keep in mind that the standard deduction for MFJ is $27,700 for 2023, so your itemized deductions would need to exceed that amount to be worthwhile. For MFS, each of you would have a $13,850 standard deduction.

Good point about checking the W-2s. Another thing to check is if either of your employers did any special bonus payouts. Those are often withheld at a flat 22% rate, which can be too low if you're in a higher tax bracket. This happens to me every year with my annual bonus.

The 30% rule of thumb is helpful! Do you think it's worth using accounting software like QuickBooks Self-Employed at my income level, or is that overkill?

For your income level ($10-15K), I think a simple spreadsheet might be sufficient if you're organized, but QuickBooks Self-Employed is actually pretty reasonably priced and automates a lot. The time you save categorizing expenses and calculating quarterly taxes might be worth the subscription cost. What I like about dedicated accounting software is that it lets you snap photos of receipts on the go and automatically categorizes transactions. It also helps track mileage if you're driving for business purposes. Plus, when your business grows, you'll already have a system in place rather than trying to transition later.

For 2025, you can deduct 67 cents per mile for business travel (the rate is adjusted annually). So if you drive 100 miles for business, that's a $67 deduction. You need to track your starting mileage, ending mileage, date, and business purpose for each trip. There are apps that can help track this automatically.

Did you write this letter yourself or have a professional help you? I'm wondering if I should add something similar but I'm not sure how to structure it without sounding like I'm making excuses.

I wrote it myself, but I followed a clear structure. First paragraph explained the events that led to my tax debt (medical crisis + job loss). Second section outlined my current financial situation with specific numbers referenced from my 433-A form. Third part detailed why my situation was unlikely to improve (permanent disability affecting earning capacity). Last section expressed my good faith desire to resolve the debt while acknowledging my limitations. Keep it factual rather than emotional. Reference specific supporting documents you've included (medical records, disability determination, etc). I also had my accountant review it to make sure I wasn't saying anything that contradicted my financial statements. About 2 pages total - not too long, but enough to tell the complete story.

This is such good advice. I missed my appeal window by 2 days and had to restart the entire process. Added 6 months to the whole ordeal. Make sure your contact info is current with the IRS too! My rejection letter went to an old address even though I'd updated everything on my forms.