I'm trying to figure out which plan will be most beneficial for me. I've always selected the PPO, but I am considering the HDHP. I understand the benefits of an HSA in general terms, but I'm struggling to do the math to figure out whether it's actually best for me.

I'm 38 years old and single. My yearly medical expenses are not astronomical, but not insignificant. In addition to preventive care, I have regular medical expenses: 3 prescription meds, a 1x/week therapist, and I see 2-3 specialists/year - I currently only have to pay low copays for all of those. Perhaps most significantly, in the past 3 years I have had about 1 large medical expense per year (e.g. an outpatient surgery, round of IVF, or an MRI). So in recent years I've hit my out-of-pocket max. Before that, I usually didn't.…