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You should gather as much info as you can regarding the prescription coverage of the plans offered, specifically around your medications and possible eligible discounts.
I do a HDHP/HSA and take an expensive medication. When the script gets ordered, the total goes towards my deductible, but my plan offers a discount for the medication which only costs me $5 every time it's filled. So literally 2 fills maxes out my out-of-pocket maximum on paper, yet only costs me $10 actual. I keep my out-of-pocket max balance in my HSA just in case something happens between Jan 1 and the time my script maxes out my deductible (4 weeks) then I roll the rest into investments. Every year.
I've had this set up with 2 different carriers.
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