re: I need help understanding all things health insurance.

You generally have 60 days to elect COBRA, which then is retroactively in force to the first day you did not have coverage. You do pay for the premium back to the first day as well.

What I have done in the past (and I have seen others do this also) is just wait until it's close to 60 days to make a decision. If you ended up needing health insurance, you can pay it and get it in force and it will be retroactive.

Of course, if you experience medical needs before the coverage is reinstated, you might have to pay up front for the health needs, and then get reimbursed by the plan.

Another option is to look at Obamacare for coverage during those 60 days.