RE: Whats the Longest you ever drove without insurance?
At least in MI it's no-fault. If you don't have insurance, and you smack your chevy into a lexus, the other drivers insurance has to cover the lexus, and you're just ##### out of a chevy. If you injure or kill someone, there are state funds that'll pick up some of your liability. I'm sure you'd still be in pretty serious trouble (you'd have a hell of a lot of trouble getting insurance too) but i don't think it would completely destroy someond financially.
Down in Detroit, there are so many people without insurance, it's unbelievable. One of the TV stations around here ran a sting on some guy down in the ghetto that was running a drive through selling fake proofs of insurance. Usually they're out there slanging rocks or something, but this guy was selling fake insurance. And business was good.
Funny you mention about getting by for a few weeks without insurance. My dad was changing jobs a number of years ago, and was without medical insurance for 2 weeks. Sure enough, he had some chest pains, and went in to get checked out. Cost like 5 grand, if i remember. Luckily it wasn't anything though.