Huckleby - you've taken a subjective survey of about 0.02% of Madison streets based on personal experience (which you don't remember accurately anyway) - this does not constitute sufficient evidence to support your idea of how parking should work, or even how it works in practice now.
Is street parking easier and better in Evanston, Illinois? There may be a larger density of cars, but that alone does not a better system make.
I apologize, Huck, for the acerbic tone I've taken in this thread. While I still believe your ideas about how parking works are completely backwards, I don't mean to convey any ill will on a personal level. I just get a little overexcited about scoring meaningless internet points sometimes.