Hey Dave, whats your opinion on the Honda Shadows? Harleys are too much, I've seen a bunch of the honda's on craigslist and they seem to be the most reasonable, 750cc. I also heard the the price break on insurance is 750cc, thats why those Honda's are technically 745cc.
Unless its been badly abused, just about any newer cruiser type bike will be essentially bulletproof. Just try to find a clean one, even better one with some service records.
Just saw this:
http://newjersey.craigslist.org/mcy/3033408737.html
Jdog has some good points, and coincidentally enough thats how I started riding. But if it's not workable here's some thoughts.
Cruisers in the size you're looking at are going to be pretty heavy bikes....
Lemme do this different.
Cruisers:
Good...
Upright seating, short ride comfortable.
Generally not abused.
Low seat height (dunno how tall you are).
Value plummets, great deals used.
Obviously the look you want.
Ok at highway speeds.
Not so good...
Heavy.
Somewhat ponderous handling.
Underbraked and softly suspended for engine size.
Ok. To be square I have something of an anti cruiser bias. I'd probably pick something with a little more brake and handling for a first bike. You want something with a little bit of power to get you out of trouble also. Remember, the big advantages of a bike on the road are acceleration and agility. And as stated, it will likely not be your last bike. But you cold do worse than a mid sized cruiser.
Look at something like a Vstrom 650 or maybe a fz6 for an idea of what I'm thinking. Honda and Kawasaki both make a 250 sporty beginner bike, which I hesitate to recommend as they are fairly anemic.
I'm all over the map here, sorry. Just trying to condense years of thoughts on this subject into something useful. So buy what makes you happy, but keep in mind how important the first bike will be in helping you expand your skills. Again, feel free to get in touch and the offer to look at something with you stands.