If you are going 250 the Ninja 250R is the way to go, unless you want the cruiser look. The Ninja is a six speed where the Rebel (and suzuki GZ250) are five,the Ninja makes the most power (34hp I believe), the ninja has better instruments including a tach, it's a DOHC water cooled motor, and it would just be more fun to ride. Oh, and it's the cheapest of the 250s available here in the states.
I think the 250 would be a lot of fun, I'd like one since I don't do much freeway riding. On the freeway it'd probably start to feel underpowered, and it'd be revving pretty high... it'd be fine for short trips on the freeway but I wouldn't want to do a freeway commute on one.