My state only charges a $50 fine per incident, if you get caught driving without insurance. So here in TN, it's no big deal if you don't have insurance. From a financial perspective, I only insure for catastrophic losses. I am more worried about being sued than I am about physical property damage, I could cover that easily. However, I have a house and a fair amount of assets so I carry liability on two cars, and comprehensive on the newer one, 2008, with a 1k deductible. I could go even higher but I am married so I don't like to push my luck with the wife.
I used to be insured through progressive and then esurance. I honestly thought esurance rates couldn't be beat until I talked with an independent broker who hooked me up with the Donegal no name insurance company. I now pay $500 per year for my cars (coverage above) and about the same for my house, which also was lower once I switched.
My advice would be to drive with insurance but only liability coverage for catastrophic lawsuits, remote as that possibility may be.