He did not make a rational decision. This is the most upsetting part. I looked. You can buy an insurance plan in Minnesota with a $750 deductable $6000 out of pocket max for $350 per month.
It is not possible with that plan and a few more like it to spend more than 1000 per month. If you are planning to spend that much anyway it is irrational to pick anything else.
What seems to have happened is he was using expensive autoinjector pens while on good insurance and then didn't adapt when he lost it and didn't get the right advice for purchasing his own insurance or the right education to be able to pick an appropriate plan.