Having been self-employed for my career, shopping healthcare annually has unfortunately become part of my job description. Having raised 4 kids (last one just graduated and hope to have fully employed/insured soon!), I am expecting my healthcare analysis to get a little simpler. To me, its about making a business decision and evaluating the risks/rewards. Barring the major catastrophes (i.e cancer), I feel like I have enough experience where I can guesstimate my annual out of pocket costs for my different healthcare buckets (i.e. dental, prescription drugs, checkups) and then also plan for the annual unknown expense (i.e. tooth implant, knee surgery, physical therapy). DW and I are both 55 and in good overall health with are biggest issues being related to old sports injuries. I hit a wall almost 2 years ago when my ACA plan as it not only became ridiculously expensive (no subsidy due to income level), but had none of our desired doctors. I did my research and decided to try a health share ministry plan. So far, I couldn't be happier with the plan and have saved over $18K/yr in premiums alone! Additionally, I can go to any doctor/health facility I choose without needing a referral! I have had 2 "claims" so far (knee injections for an old ACL injury and a broken foot) that totaled approximately $12K - $15K in costs and I paid essentially zero out of pocket after reimbursements. I am fortunate that I have significant resources to cover out of pockets which weighs into my risk/reward analysis, but I also can look back and say I am over $18K ahead after 1 year on the plan.
As the rules and options continue to change, I will continue this strategy of doing an annual assessment as before in hopes this bridges the gap until 65. From what I have read, if the SHTF and I came down with a ridiculously expensive condition and my health share plan just didn't provide the expected coverage (no reason to believe that yet), I could bail and go back on ACA, even at the higher premiums as that might be the better business decision at that time.
No one size fits all, but that's my plan (and has been my plan for 31 years) and until I find a better mousetrap, will run accordingly.