Only you can choose what's right for you. All I can say is that I've never met anyone who after a few years, looks back and says I'm glad I sold my 250 when I did. To a person, it's "I made a mistake and should have kept it much longer". Anything you need to learn about riding on the street the 250 can teach you. Style's a personal thing, and the older-gen does have an old-school look to it, but I think someone who's riding the crap out of an older bike has more going for them than someone tip-toeing and wobbling through the corners on the latest and greatest repli-racer...