I would look at your intended use for the bike:
around town I would stick to the 250.
highway something else bigger would be better.
cruising or riding sporty fashion?
Long distance or short distance?
Etc- these could decide what would suit you. E.g. I bought a GT550 the other day coz it was cheap- did a 2000km weekend on it last weekend- best bike I have ridden on that sort of trip- even better than ZZR1200 for touring believe it or not.(more comfy and licence friendly) Great on fuel- (well over 400km to a tank 21.5L), comfy as, sounds good, basic, solid engineering- air cooled so no stuffing around with radiators and the like, shaft drive- maintenance free (well I did change the diff oil which took no more than ten minutes) etc etc.
$1500-2000 will get you a pearler and will last you forever- mine has 160000km or 260000km on it and it doesn't even blow smoke or use oil.

It's no sportbike, but it's other attributes make up for that. Did I mention I did 2000km in a weekend TWO UP...still got 20km/L fuel economy.
