Great discussion here! One additional thing to consider that I haven't seen mentioned - make sure you have solid documentation of your residency periods for both properties. The IRS can be pretty strict about proving the "use test" especially when there are overlapping ownership periods. I'd recommend gathering utility bills, voter registration records, driver's license addresses, and any other documentation that clearly shows which property was your primary residence during specific time periods. Since you both owned separate homes before marriage, you'll want to be extra careful about demonstrating continuous primary residence use. Also, if either property was ever rented out (even briefly), that could complicate the exclusion calculation. The IRS has specific rules about periods of "nonqualified use" that can reduce your exclusion amount. Worth double-checking your timeline to make sure there weren't any rental periods you might have forgotten about.

One thing that hasn't been mentioned yet is the timing consideration for your sales. Since you're married now, you'll want to be extra careful about which tax year each sale falls into, especially if you're considering filing separately. If you sell both properties in the same tax year and file separately, you'll each need to report your respective property sale on your individual return. However, if you can time the sales to fall in different tax years (one in December 2025, one in January 2026), you might have more flexibility in choosing your filing status each year based on what's most advantageous. Also, don't forget about depreciation recapture if either of you ever claimed a home office deduction on these properties. That portion of the gain isn't eligible for the Section 121 exclusion and will be taxed at a 25% rate regardless of your filing status. I'd strongly recommend running the numbers both ways (MFS vs MFJ) with a tax professional who can model different scenarios, including the timing of the sales. The capital gains exclusion benefit might be offset by other tax disadvantages of filing separately, depending on your overall financial picture.

Has anyone ever had the IRS challenge their treatment of earnest money in a 1031? I'm in a similar situation but worried about getting flagged for audit if I don't report it as ordinary income.

This is such a complex area and I'm seeing some really helpful insights here! As someone who just went through a similar situation, I wanted to add that documentation is absolutely critical. I kept detailed records of the first buyer's breach of contract, the earnest money forfeiture, and how it related to my overall 1031 exchange timeline. My tax preparer said having clear documentation showing the connection between the earnest money and the eventual successful sale was key to justifying treating it as part of the overall transaction rather than separate ordinary income. One thing I learned is that if there's a significant time gap between losing the first buyer and closing with the second buyer, the IRS might be more likely to view these as separate events. In my case, the gap was only about 6 weeks, which helped support treating it as one continuous transaction process. Also worth noting - if you're doing your own taxes, Form 8824 for the 1031 exchange should include all the transaction details, including any adjustments for earnest money situations like this. Don't forget to adjust your basis calculations accordingly!

Aaron, based on all the discussion here, it really sounds like MFS is your best bet given your PSLF timeline. Just wanted to add one more consideration - make sure you document everything when you switch filing statuses! Keep copies of your tax returns, any correspondence with your loan servicer, and track your qualifying payment counts carefully. I'd also suggest reaching out to your loan servicer BEFORE you file to let them know you're changing from single to MFS. This way they can update your payment calculation as soon as your new tax info is available, rather than you having to chase them down later like some folks mentioned. With only 12-15 months left until forgiveness, you're in the home stretch! The temporary payment reduction from filing separately will definitely be worth more than the tax benefits you're giving up. Just make sure both you and your wife understand which deductions each of you can claim so there are no surprises come tax time.

Aaron, based on all the great advice here, filing MFS with your wife claiming the house definitely seems like the right move for your situation. The $960 difference ($1,389 vs $425) is significant, especially with PSLF so close. One thing I'd add - make sure you submit your updated tax info to your loan servicer ASAP after filing. They often take 2-3 months to process the change, and you want to maximize those lower payments before forgiveness kicks in. Also, keep detailed records of everything since servicers can be... challenging to work with. Since you're in Pennsylvania, the state tax impact should be minimal given their flat rate structure, but definitely double-check those numbers too. You're in a great position with PSLF almost done - this filing strategy should help you squeeze out every bit of savings in these final months!

I'm dealing with a similar situation right now! I've been legally blind since childhood but only recently learned about the tax benefits. One thing I'd add is that if you're employed, you might also want to look into whether your employer offers any vision-related benefits or accommodations that could have tax implications. Some assistive technology purchases for work can be deductible as unreimbursed employee expenses if you itemize. Also, I discovered that if you use a tax preparer, many of them aren't familiar with these specific deductions for blindness. When I went to H&R Block last year, the preparer had to look it up because they'd never handled it before. So don't feel bad about not knowing - even some tax professionals miss this stuff! It might be worth specifically asking your preparer about disability-related deductions when you file going forward.

Great question about assistive technology deductions! From my experience, items like screen readers, braille displays, and voice recognition software can potentially qualify as medical expenses if they're primarily for managing your blindness, but the rules are tricky. For work-related equipment, it depends on whether your employer reimburses you and whether you itemize vs take the standard deduction. The key thing with assistive technology is documenting that it's "primarily for medical care" - so if you use a braille display 80% for managing daily tasks related to your blindness and 20% for general computer use, it would likely qualify. But if it's mainly for general productivity, it might not. One thing that helped me was getting a letter from my eye doctor specifically stating that certain equipment is medically necessary for my condition. This creates a clear paper trail if the IRS ever questions it. Also, keep detailed records of how you use each piece of equipment - the IRS may want to see that it's truly medical in nature rather than just convenient technology. You're absolutely right about asking your CPA to review past returns! Many tax professionals don't specialize in disability-related deductions, so being proactive about bringing this up could uncover missed opportunities. There are often multiple angles beyond just the standard deduction - medical expenses, equipment costs, sometimes even transportation expenses related to medical care.

Just a heads up that if you refinanced last year, you might have TWO 1098 forms - one from each lender. Don't forget to add both when calculating your total mortgage interest! I almost missed this and would have underreported by $3,200.

Another thing to watch out for - if you paid any points when you got your mortgage, those should show up in Box 6 of your 1098. Points paid on a purchase mortgage are generally fully deductible in the year you bought the house, which could add a nice chunk to your itemized deductions. Since you bought in August, you might have paid origination points that you can deduct this year. Just make sure you didn't already deduct them if they were rolled into your mortgage amount rather than paid separately at closing.