What tax strategies can a high wage W2 HENRY use to lower taxes in 2025?

Thanks for the welcome and advice! I didn't know HSAs were triple tax-advantaged - that sounds really helpful especially with our daughter's ongoing therapy costs. Do HSA contributions count against our 401k limits or are they completely separate? Also, do you know if therapy for developmental delays qualifies as a medical expense for HSA purposes?

HSA contributions are completely separate from your 401k limits, so you can max out both! For 2025, a family can contribute up to $8,300 (plus $1,000 catch-up if you're 55+), and this is on top of whatever you put in your 401k. Yes, most therapy for developmental conditions qualifies as a legitimate medical expense for HSA purposes. This includes occupational therapy, speech therapy, physical therapy, and specialized educational therapy when recommended by a physician. Just make sure to keep good documentation from healthcare providers stating the medical necessity.

I'm a bit skeptical about AI tools for something as important as taxes. How accurate was it compared to having a human accountant review your stuff? Did you have any issues with the IRS afterward?

Does it work for people who are self-employed too? I have W2 income but also do consulting on the side and my tax situation is kind of a mess because of it.

It was actually more accurate than my accountant in some ways. The platform doesn't replace human judgment - it just identifies opportunities that might be missed. I still had my accountant implement the strategies, but armed with the AI's suggestions. No issues with the IRS at all since everything was legitimate deductions and credits - just ones that are often overlooked. Yes, it actually works extremely well for mixed income situations! It's particularly good at finding deductions for self-employed people and identifying which expenses can be allocated between business and personal use. I have a friend who's a W2 employee with a side business, and the platform helped her properly categorize her home office and vehicle expenses to maximize legitimate deductions.

That's really interesting - I've tried calling the IRS a couple times and gave up after being on hold for over an hour. How much does this service cost? Is it worth it compared to just working with a tax professional directly?

This sounds like a scam. Why would anyone pay a third party to call the IRS when you can just do it yourself for free? And the IRS agents often give conflicting advice anyway - I've called multiple times with the same question and gotten different answers.

The value really comes from the time saved and getting definitive answers. For me, the peace of mind knowing I was getting official guidance directly from the IRS was worth it, especially for something as complex as special needs tax planning where a mistake could trigger an audit. I completely understand the skepticism - I felt the same way initially! But after three failed attempts calling the IRS myself (each time waiting over an hour before having to hang up for work or family reasons), I realized my time was worth something too. The service just makes sure you're connected quickly instead of waiting on hold. The actual tax advice comes directly from IRS agents, so it's the same information you'd get if you managed to get through on your own.

This sounds interesting but I'm not following completely. Wouldn't you end up with the same deduction amount over the two-year period whether you bunch them or not? What's the actual tax advantage?

The advantage comes from occasionally getting to itemize when you otherwise wouldn't. Here's a simplified example: Say the standard deduction is $30,000 for a married couple, and each year you have $28,000 in potential itemized deductions. If you take those deductions normally, you'd just claim the standard deduction of $30,000 each year (total $60,000 over two years). But if you bunch two years of deductions together, you could have $56,000 in itemized deductions in Year 1, then take the standard $30,000 in Year 2. That's a total of $86,000 in deductions over the same two-year period - a $26,000 difference! This works especially well with charitable donations since you have control over their timing.

Real estate is great in theory but the headaches of being a landlord are real! I tried this route and ended up selling after two years of tenant nightmares. Maybe I just had bad luck though. Did you go with single family homes or multi-unit properties?

I totally get the landlord concerns! We actually use a property management company that handles all tenant interactions - well worth the 8% fee for the headache reduction. We have two duplexes and one single-family home. The duplexes perform better from a cash flow perspective, but the single-family has appreciated more. If you want the tax benefits without the landlord hassles, you could look into real estate syndications or REITs, though the tax advantages aren't quite as strong as direct ownership. The key is to work with a tax professional who specializes in real estate investors - they know all the strategies that regular CPAs often miss!