Is there really a significant tax benefit to keeping my mortgage?

So does that mean if I'm married and our total itemized deductions are like $25k, we're still better off taking the standard deduction of $27,700? And if that's the case, would I actually save more in taxes by just paying off the mortgage completely since the interest isn't actually providing any benefit?

Yes, in your scenario if your itemized deductions total $25k, you'd be better off taking the standard deduction of $27,700 since it's higher. You'd save $2,700 more in deductions that way. Regarding paying off your mortgage, from a purely tax perspective, if the interest isn't providing any deduction benefit, then yes, you wouldn't be losing any tax advantage by paying it off. But remember that mortgage decisions should consider other factors too - your interest rate, investment opportunities for that cash, emergency funds, etc. The tax aspect is just one piece of the puzzle.

How secure is it to upload all your tax documents to some random website? Seems risky just to get an answer about mortgage interest. Couldn't you just ask your accountant?

Does it work for rental properties too? I have both a primary residence and two rental properties, and I'm always confused about how the mortgage interest works differently for each.

They use bank-level encryption and don't store your documents after analysis, so it's actually very secure. I was hesitant at first too but read their privacy policy. And honestly, I don't have an accountant - that's part of why I was looking for tools to help me understand this stuff better. For rental properties, absolutely! The tool specifically pointed out that my rental property mortgage interest was deducted as a business expense on Schedule E, completely separate from the itemized deduction question. It showed exactly how much tax benefit I was getting from each property's mortgage interest.

How does that even work? The IRS phone lines are notoriously impossible to get through. Is this just paying someone to wait on hold for you?

Sounds like a scam honestly. Why would anyone be able to get you through to the IRS faster than just calling yourself? The IRS doesn't have some special line for certain people.

It uses a system that navigates the IRS phone tree and holds your place in line. When an agent is about to pick up, you get a call connecting you directly to them. So yes, it's basically a sophisticated way to wait on hold without you having to sit there listening to the hold music for hours. No, it's definitely not a scam. They don't ask for any tax info or personal details beyond your phone number to call you back when an agent is ready. I was skeptical too but was desperate after wasting so many hours trying to get through myself. The IRS has different departments and phone trees - this service just knows how to navigate them efficiently.

That's a really good point I hadn't considered! My property taxes are around $8k, and with state income tax on top of that, I'm definitely hitting that $10k SALT cap. Maybe that's partly why my mortgage interest doesn't seem to be helping at all with my taxes. Would you say it made sense for you to keep your mortgage or are you considering paying it off too?

I'm in a similar position to you - considering whether to keep or pay off my mortgage. For me, the math works out that I'm getting very minimal tax benefit from the mortgage interest. I'm getting maybe a $1,000 extra deduction from itemizing versus taking the standard deduction. At a 24% tax bracket, that's saving me about $240 in taxes while I'm paying far more in interest. I'm actually planning to pay off a significant chunk of my mortgage this year. Not the whole thing, but enough to reduce my interest to the point where I'll just take the standard deduction going forward. The psychological benefit of having a much smaller mortgage outweighs the tiny tax advantage for me.

That's actually a really good point about inflation. I never thought about it that way. $300k today will be worth a lot less in purchasing power 20 years from now, but you're still paying it back with those cheaper future dollars.