I face a similar dilemma in that my 250, which I really love so far, was bought second-hand and has quite a few cracks/scratches and other mishaps in the fairings.
While it runs fine, fixing the cosmetics would run up to quite a bit of money…and wouldn’t be very logical for my first bike.
However, there simply aren’t any other bikes below the 600cc mark that appeal to me the ninja stands alone.
It seems a waste of money to trade in a 250 for a newer, practically the same 250 (minus the itty bitty damages)
However, the only step up, for sportbikes as far as I know, are the 650’s which are a lot more expensive to buy and maintain, *shudder insurance*, and probably too powerful for someone like me.
Regardless, I’ll see in a season if I would keep it or move up. Or if they bring the FI 250 stateside. (a little bit more power wouldn’t hurt either)