I ahve been thinking used, and still giving it some thought, just sorta want to treat myself on this one. And avoid picking up someone else's problems. Never bought myself a new car, and good chance a I never will(hope to be married by time I need to replace my truck, and then I expect I'll do things way my parents did, where I'll always have a used car and will buy the new, and hopefully, more reliable, vehicle for my wife so she doesn't have to worry about things). Also, since I don't know bikes as well as I know cars/trucks(though I'm sure going to learn), dont' trust myself to be able to identify any potential problems with a used bike. If I lived clsoer to my aprents, would bring my dad along shopping and consider used, but the 850 mile gap makes for a bit of a drive too pick him up.
Sure I'll buy other bikes in future, heck, I count on it.

To help put that off fo ra while though, is why i decided on the 750/800 class cruisers. I wanted a bike I could take on road trips(aforementioned 850 miles is main one), but that was not too big for a starting bike. So that knocked out anything 1000cc and above. Gave some thought to a smaller bike, as a 250 or 600 really might be better to start, but only one I really gave thought to was the Honda VLX(584cc), but with only a 4 speed, just can't see it(and reviews seem to agree) really making me happy on road trips, which means I'd be looking to replace it after first trip, which would end up costing me more in long run.
I definitely will ask around for local shops though at safety class, and have a guy here at work who I'm sure would help me, and works on everything from the Vespa who's pistons he jsut reringed to a large variety of Fords. Great guy, and sure he'd help me.
Heck though, buying a new bike, bewsides a first check of the valves after a few hundred miles, shouldn't be too much maintenance wise as llong as I stay on top of oil changes.
I do expect thought hat on next bike, and any after that, will buy used and take care of my own wrenching, just like I do on cars now(least, for most things)