HDHP vs. PPO/OAP plan Question…is growing an HSA worth the cost of paying max OOP w/ chronic illness?

I also posted this in r/personalfinance, but didn’t get many responses. It’s open enrollment at work, and I was just diagnosed w/ a chronic illness about 2 months ago. Approaching 40, good salary (approx 110K), not in the best position w/ retirement savings (@ 50K in 401Ks and 25K in a Roth) and wanting to take better care of future me. So, here’s the numbers I’m working with (for an individual plan).

HDHP: OOP max – $5000 + premiums @ $1,800 annually = $6,800 …With new medication costs, plus a couple other scripts, I will definitely hit OOP max. Deductible is $3200, but I don’t think that really matters since I know I’ll hit it.

PPO plan – OOP max 4,500 + premiums @ 3,300 annually = possibly up to $7,800 annually. Prescription co-pays don’t count towards deductible anyway. Based off the drug formulary for monthly scripts, I’m looking around 500-1000 on the year for rx/doc appt. co-pays. So, best case scenario I spend around $4,500 pre-tax dollars on the year (would use an FSA to cover copays, etc.) Deductible is $1,500.

With the HDHP, I can contribute up to $4,150 into an HSA, automatically taken from my pay-check (no employer contribution). I know without question that I will obviously pay way more this year for medical costs for the HDHP (basically 5,000 post tax and $5950 pretax). BUT…is the long term gain on the HSA funds appreciating over time worth the additional costs this year? I don’t know how to do that kind of math. I assume older me will almost certainly have unexpected/expensive medical costs. How many years do I need that money to invest before I ‘break even’ on the additional cost I’m spending now? Does that question even make sense?!

I’m fortunate to be in a position where I am able to save around 1K/month after monthly expenses and 401K deductions. I try to just plunk the max into a ROTH from my savings before the April deadline. I’m almost certain (pending out-of-network emergency medical disaster!) I can pay the approx. 10K in medical costs this year and still pay off the rest of my 11K in student loans. It would mean eating into my emergency funds a bit and probably only having 7-8K in emergency funds to work with…but also mean being 100% debt free w/ a little starter HSA as well as my Roth and 401K. Sooooo….any mathletes in here have advise/words of wisdom? Things I haven’t considered that I should be thinking about? Math formulas I can use to help me understand my options? Is paying more in medical expenses now, while I can afford it, worth the potential HSA growth later????

If you’re still reading…thank you 🙂