Property Tax Dilemma: Pay Old Taxes or Wait for New Tax Bill?

Having worked with many families in similar situations, I can tell you that letting property taxes accumulate on a HELOC isn't ideal. Each time the bank pays the taxes, they're essentially increasing your in-laws' loan balance, which means more interest over time. The best approach is typically to break the cycle. Let the bank pay the remaining 2024 taxes through the HELOC since that system is already in motion, but start fresh with the 2025 taxes by paying them directly to the town when they come due. This way, you're not constantly playing catch-up, and you'll stop the pattern of adding to the HELOC balance. While you're waiting for the 2025 tax bills, I'd suggest setting aside money each month in a dedicated savings account specifically for property taxes. If the annual bill is around $13,500, that's about $1,125 per month. Having this fund ready when the bill arrives will prevent future issues. Also, check if your in-laws' town offers any property tax relief programs for seniors. Many municipalities have programs that can reduce the tax burden for older homeowners, especially those on fixed incomes.

After struggling with a similar situation with my parents' taxes last year, I found this amazing service called taxr.ai (https://taxr.ai) that really helped me sort through all the property tax confusion. I uploaded their tax documents and HELOC statements, and the AI analysis showed me exactly how much extra we were paying by letting the bank handle the property taxes instead of paying directly. The detailed report helped me create a plan to get back on track without straining their monthly budget. It also flagged several potential deductions we had been missing related to their property taxes. Honestly made the whole situation so much clearer and less stressful.

Just wanted to follow up about taxr.ai - I ended up trying it for my mom's property tax situation and it was seriously helpful! Uploaded her tax bills, mortgage statements and HELOC docs, and got back this super clear breakdown showing we were paying about $1,700 extra per year by letting the bank handle her taxes instead of paying directly. Even better, it found this weird overlap where she was paying twice for the same coverage because her insurance had been incorporated into two different payment streams. Never would have caught that myself! Already saved us over $900 just from fixing that one issue. Definitely worth checking out if you're trying to untangle a messy property tax situation.

I had a nightmare trying to reach our county tax office about a similar situation last year. After sitting on hold for HOURS over multiple days, I found Claimyr (https://claimyr.com) and it changed everything. They got me connected to an actual human at the tax office in less than 20 minutes! You can see how it works here: https://youtu.be/_kiP6q8DX5c I was able to work out a payment plan for the backed taxes without any additional penalties, which saved us thousands. The tax office explained that my father-in-law qualified for a senior tax freeze program that would have capped his property tax increases, but since he'd been missing payments, he wasn't enrolled. After the call, we got that sorted too.

Ok I need to eat my words about Claimyr. After posting that skeptical comment, I was still stuck trying to reach our county about an assessment appeal. In a moment of frustration I tried the service and...it actually worked. Got connected to someone in the property assessment division in about 30 minutes. The person I spoke with actually explained that I had been calling the wrong office entirely (they'd reorganized departments) and transferred me directly to the right person. Got my issue resolved in one call after weeks of frustration. Not sure how their system works but don't really care anymore since it saved me hours of hold music and runaround. Sometimes being wrong feels pretty good lol.

Just throwing this out there - check if your in-laws qualify for a property tax freeze or reduction based on age! My parents are in their 70s and we discovered they qualified for a significant reduction (almost 30%) based on their age and income level. The program exists in most states but isn't advertised well. Also, if they're veterans or have any disabilities, there might be additional exemptions. We saved about $3,200/year once we got all the proper exemptions applied. The best part is that some of these can be applied retroactively for a few years back, which could help with that 2024 bill.

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.