My bike history so far :01 vt250-->1989 Cbr 250r (MC19) -->2009 Ninja 250r-->2010 Ninja ZX10R (we all gotta grow up sometime)
Anyways......
Got rid of the VT because it was heavy and slow and just got bored of the whole cruiser look, noone's gonna think you're a bad ass bikie with a 250cc. So moved onto the CBR. Awesome bike, but it was old, and like EG52NV said unless you're revving the nuts off the thing it's gonna feel and more importantly be slow. That one lasted me about 8 months, paid 3500 and got 3000 trade in on it (pretty good i thought), and i ended up with the Ninja 250. Those things are fun at pace. Carried my fat ass around with no problems. I think that they're the best 250cc out on the market out today. Even better than the current CBR250r (flame suit on). They look good, go ok for what they are, they're all over the place in second hand market so you shouldn't have any trouble finding one in decent condition, but yeah depends what you want to spent. And finally after getting bored with the 250's i ended up trading in the little ninja for a bigger ninja, but that's another story for another thread.

Knowing what i do now, i wouldn't bother with the 250's, especially if you're going to keep it for longer. There are so many 400, 500, and 650cc bikes out there that are lams approved, both new and second hand
I ended up letting my 250 ninja go for 3000, needed a major (24000) service and few other bits and pieces, but otherwise a solid little bike



That's just my 0.02, hope it helps and good luck. Keep us posted