In reviewing the details of my situation, is it the opinion of the community that I should be able to win this in small claims court?
As I wrote previously: "It sounds like the deal was for the car and the tranfer of warranty for whatever you paid for it. The seller delivered the car but not the warranty. You're entitled to the benefit of the bargain, so I think you probably have a strong claim for either the cost of the warranty or a refund (or outright rescission of the deal)." I'll leave it to you to combine what I wrote with what others wrote to decide what "the opinion of the community" is.
Is my printout of the Craigslist ad sufficient? or should I request a copy direct from Craigslist after I file?
I don't understand the distinction you're drawing, but I imagine your printout should be sufficient unless the other party claims you've altered the ad in some way.