I can't comment on much because I'm no expert, however my understanding is this:
To be a Free man on the land you need to cancel your drivers licence, health card, SIN card to revoke your citizenship to Canada.
What I am an expert on is insurance. Without a valid Ontario drivers licence and without an vaild Ontario vehicle ownership, you will not be able to obtain insurance. I only say this because you said "I'll always have some form of insurance that's just good financial sense". I agree.
If a free person on the land causes injury to someone in a vehicle collision, the full financial responsibility of that; rehabilitation costs for the other person and their passengers, damages to their vehicle, their lost wages, damaged property, etc.. rests fully on his/her shoulders. This is not how it goes if you are insured; the other drivers policy picks up most of those costs, but since you don't pay into the insurance system; a pooling of the money of the masses to pay for the losses of the few, they hang your "free man's" ass out on a line and let you pay your own soverign way. But hey, you dodged a few fines along the way so you can afford it, right?