1 - Insurance premiums from employer provided insurance are essentially tax deductions. In other words if you pay $10k in insurance premiums and your marginal tax rate is 30%, you’re really only paying $7,000 in premiums. If you buy health insurance on your own you lose this tax benefit.

2 - All you can do is guess at your health expenses. If you’ve got someone with major health issues, planned surgeries, or your wife is pregnant, that part is easy. Otherwise I usually assume my kids are each gonna incur about $600 or so from being sick, stitches, etc. You may have a good sense at this point on what the costs are on average.

3 - Unfortunately it is pretty difficult to get information on what other companies offer until you actually have a job offer.

4 - You may want to consider checking out some of the Christian health share providers. Just reminder that premiums won’t be tax advantaged, you won’t be able to contribute to an HSA, and you are taking a gamble that they will cover everything.