Regarding new vs. used: I believe it was Soren who said the best year and model so far is the 2007 Speedmaster. Of course he is biased but I tend to agree. If I lost my 2002 America for whatever reason, that's what I would look for (if I wanted to replace it and didn't just "step up" (oh no I didn't!) to a Rocket III). All it's missing is spoked wheels, but I don't mind the directional alloys and that can be "fixed" for not a lot of money if you're willing to go single disc front.
