I'm dealing with a very similar situation right now - sold my primary residence in November and bought a new one in August, so I had overlapping mortgages for a few months. The mortgage interest calculation has been giving me nightmares! After reading through all these responses, I think I'm going to try the simplified average balance method that @Margot Quinn mentioned. It seems like the most straightforward approach and my tax software should be able to handle it easily. One question though - when you're calculating the average balance, do you include the principal payments made during the year or just use the outstanding balance at the end of each month? I want to make sure I'm doing this correctly before I file. Also, has anyone here actually been audited on this specific issue? I'm curious if the IRS really does scrutinize the calculation method or if they're more concerned with whether you're claiming too much interest overall.

I went through this exact scenario two years ago and learned some hard lessons that might help you avoid my mistakes. The key thing I wish I'd known upfront is that you need to be super careful about how you track the dates and balances. When I first tried to calculate this myself, I made the error of using my closing dates instead of the actual months I was making payments. The IRS looks at when you're actually obligated to pay interest, not just when you technically owned the properties. So for your September overlap month, make sure you're only counting the interest you actually paid on both mortgages during that specific period. Also, keep detailed records of every payment you made. I ended up having to reconstruct my payment history from bank statements because my mortgage servicer's year-end statement didn't clearly show the month-by-month breakdown I needed. It was a nightmare during tax prep. One more tip - if your new mortgage had any points or origination fees, those might be deductible separately from the regular interest, but they have their own rules about whether you can deduct them all in year one or need to amortize them over the life of the loan. Don't forget to check on that piece too.

Has anyone had luck filing with a substitute W-2 (Form 4852)? My employer went out of business in November and I can't get anyone to respond about my incorrect W-2. I have all my pay stubs but I'm nervous about using the substitute form.

I'm dealing with almost the exact same situation! My Box 2 is showing $0 even though I had federal taxes withheld all year. I checked my final pay stub and it shows over $3,800 in federal withholding, but my W-2 has nothing in that box. I contacted my HR department yesterday and they're saying it might take 2-3 weeks to issue a corrected W-2. I'm getting worried about the filing deadline since we're already in April. One thing that's confusing me though - when I look at my online payroll portal, all my pay stubs show the federal tax deductions, but when I add them up manually, I get a slightly different total than what my final pay stub shows as YTD. Has anyone else noticed small discrepancies like this? I'm wondering if there were some adjustments made that I'm not seeing. @Aria Park - definitely don't file until you get this resolved. I made that mistake once before with a different tax issue and it created a huge headache with the IRS.

Has anyone mentioned the tax implications? When property taxes are paid through a HELOC, they're not automatically deductible on income taxes like they might be if paid directly. You have to itemize the HELOC interest correctly. Make sure whoever does their taxes knows about this situation!

I've been through something very similar with my elderly parents, and I'd definitely recommend breaking the HELOC cycle now rather than later. Here's what worked for us: First, contact your town's tax collector office directly to get the exact balance owed for 2024 and ask about payment plan options. Many municipalities offer interest-free payment plans for seniors or families dealing with financial hardship - this could save you hundreds in penalties. Second, definitely look into all the senior exemptions others have mentioned. Beyond veteran benefits, many states have "circuit breaker" programs that limit property tax increases for seniors on fixed incomes. Some also offer deferrals that let seniors delay tax payments until the property is sold. The key insight I learned: every month you let the HELOC handle this, you're paying compound interest (HELOC rate on the tax amount plus any municipal penalties). We calculated we were losing about $200/month by not addressing it directly. I'd suggest calling the tax office first thing Monday morning - in my experience, they're actually quite helpful when you explain you're managing elderly parents' finances and want to get caught up. They may even waive some penalties if you show good faith by setting up a payment plan.

Another factor that could explain the difference is if you have student loan interest deductions. If you're paying student loans and she isn't, you can deduct up to $2,500 in student loan interest, which would reduce your taxable income and potentially explain part of that $1,350 refund difference. Also worth checking if either of you contributed to a traditional IRA during the tax year - that's another above-the-line deduction that reduces taxable income. Even a $1,000 IRA contribution could create a meaningful difference in your final tax liability compared to someone who didn't contribute.

This is a really common situation that confuses a lot of people! The key thing to understand is that a refund isn't necessarily "good" - it just means you overpaid your taxes throughout the year. Your coworker who owes $15 actually had her withholding dialed in almost perfectly. Looking at all the responses here, it's likely a combination of factors: your 401k contributions (which reduce taxable income), different health insurance situations, student loan interest deductions, and possibly different W-4 setups. The 8% 401k contribution you mentioned is probably the biggest factor - that's over $5,000 less in taxable income compared to your coworker. If you want to get more money in your paychecks instead of waiting for a big refund, consider updating your W-4 to account for these deductions. The IRS withholding calculator can help you figure out the right amount to have withheld so you break even (or close to it) next year.

Just a heads up - don't forget to consider state filing requirements too! Depending on your state, you might need to file additional self-employment forms at the state level. I learned this the hard way last year 😭

I'm in almost the exact same boat - W-2 from my day job plus a 1099-NEC from some freelance work I picked up. After reading through all these responses, I'm definitely leaning toward checking out FreeTaxUSA instead of paying the premium for TurboTax Self-Employed. One thing I'd add is to make sure you track any business expenses related to your 1099 work - things like equipment, supplies, mileage, or even a portion of your internet bill if you worked from home. These can really help offset the self-employment tax burden. I wish I had been better about tracking expenses throughout the year instead of scrambling to remember everything now at filing time. Thanks everyone for sharing your experiences - this thread has been super helpful!