I don't know whether schools and career centers cover this topic much, but they should.
P.S. As I've commented before, it's not just about you. It's also a matter of protecting loved ones, who may feel compelled to spend their assets caring for you if something unfortunate and expensive happens to you. In that sense, even if you don't have money to pay the deductible amount yourself, a high deductible policy can make sense in that your family may be able to help you financially to that extent, while the insurance protects against the really big bills (and also, as others have noted here, negotiates lower charges for services so that you don't pay the ironic/perverse "highest possible costs" that the uninsured often face due to lack of negotiating power).