I'd like to get a small used cruiser. In my research so far I've really liked the Rebel 250 (good size, price, reliability, and I like how it looks), but from what I've read I'm worried I'll be too cramped on it. I'm about 6'2" tall, 150 lb, roughly 31" inseam (this is me wearing a ridiculous-looking clean room suit). I can deal with being a little bit confined; my current vehicle is a small Honda civic which I'm quite comfortable in, though some of my similar-height friends can't stand it. I'm more worried that my knees will sit ridiculously high and possibly interfere with safe riding. Any suggestions on bikes that are similar in style and (more importantly) cost to a used Rebel 250, but may accommodate my height?
I'd also like to know what sort of things I should check when I'm looking for used bikes. I'm pretty mechanically apt with purchasing used cars, and do most of the minor maintenance on my vehicles. I just don't have any reference point with motorcycles because none of my family or friends ride one! I'd like to keep the cost of the bike as low as possible, but I don't want to buy something on its last leg of life which will require constant repair. What sort of mileage is considered a reasonable lifetime for a small, well-maintained cruiser? What kinds of things might I expect to repair/replace on an older bike?
Any other advice you want to offer for a new rider is much appreciated. I fully intend to invest in and always wear all the safety gear as I have no interest in screwed up skin or bones or death for that matter.

Thanks a lot for your help!