I work in a healthcare adjacent business and while there is a large amount of information out there and a lot of market participants it isn't nearly enough information to make an informed decision. Whether a drug you currently use will be reimbursed at your local pharmacy and about what your out of pocket cost will be is entirely opaque to the consumer - it's even opaque to drug manufacturers and, in many cases, the precise cost is opaque to insurers until the pharmacy actually states their fill cost to the insurer for reimbursement - and these charges are arbitrary and continuously in flux.

When shopping for individual insurance you're trying to balance a lot of future unknowns - will you puncture your kidney in the next year and need dialysis? How likely is it and how much is 50% POC (Price of Charge) coverage worth to you? Are you going to need an oncological drug due to a sudden cancer diagnosis - those can easily run into the hundreds of thousands of dollars a month - I hope you don't accidentally choose an insurance that covers treatment for all variants of cancer except the one you need treated.

The health insurance market is insanely opaque and most employers pick a reasonable plan and, when that plan inevitably refuses to cover a necessary procedure for their employee - they bitch and moan at the company over the phone and leverage their collective bargaining. There are also some really good reasons that the ACA didn't extend the individual market as a replacement for medicare since those insanely expensive and obscure treatments get more likely as you age.

Right now we're sorta surviving on insurance supplemented by go-fund-me and good will but that's a terrible system. Sudden insane health expenses can happen to you - I hope they don't, I wish they didn't happen to anyone - but our current system treats most folks decently well and really screws over a select few, and not due to any particularly stupid decisions on their part in most cases.