I was always a new car buyer until my first Insight, and then I was so happy with the bang for the buck on the used Insight I purchased (from a Dodge dealer, no less) that I convinced my girlfriend to do the same and we are both equally happy. We got hers from private sellers. We met them (duh!) and they are really nice people and took great care of their Insight (they named her Jane, in fact). We kept her name in honor of them, in fact.
You need to learn a bit about what to look for and figure out if the seller is a crook or not (for the GF's car, I first was involved in trying to buy one from what turned out to be a crook named 'Maurice' down East of LA), but after that it's wonderful to have the car.
If I had not gone to the 2nd hand market, I never would have been able to get one (I wanted a manual) and we got such good prices that we have two for the price of one and neither has had any problems other than a busted rear wiper nozzle which cost $50 to have fixed at the dealer.
You can also get a Honda warranty, which you can cancel at any time and get your pro-rata cash back, if you worry.
I vote to keep your eyes on the second hand market, and at least talk to some sellers. If they aren't local, you can then decide if it is worth the trip.
A lot of folks here have flown out to their sellers, and driven back. I don't know if anyone has had a problem yet doing that.