Originally posted by: ValValline
In that price range your best option is a Ninja 250R for something newer (5+years old). Performance wise it totally outclasses and embarrasses the other 250s our there. The seating position is not aggressive, and more like a standard than a sportbike. They are a blast to ride and you get to work the whole RPM range while still staying within sane/legal speeds. Also it is fully capable of freeway speeds unlike the other 250s (rebel virago etc) that need a good tailwind.
Other than that other good options are older GS500s (same basic bike as the newer fully faired GS500F, but naked with a round headlight), Ninja 500Rs, Buell Blast, or Honda 750 Shadows. Finding these bikes for around 2K may be a bit tougher. At that price range they tend to have some hard miles on them, but they are all solid machines.