I started on a 92 Honda CBR F2 600. Never been on one before, or even a dirt bike for that matter. It lasted me about a year, then I got a 98 F3 600. now on a 02 F4i You learn alot riding on older bikes, and really appreciate the advancement they have made when you move up to newer and better. Its not hard to learn at all, whats harder is learning how to pay WAY MORE attention to everyone else around you. Honestly, the 250 isnt a bad idea, but I wouldn't disagree with starting on an older honda like I did. You don't have to upgrade as soon, you will be learning on something more similar to what you will be riding in the future, and as long as your smart, you will be ok. Definitely make sure you have money for riding gear in your budget when you pick your bike. you need FOR SURE, a quality helmet, AGV, HJC, KBC. nothing outrageous. Just a quality product. and a good set of gloves and a jacket. You will be going down. Its guaranteed, don't know when, but you will. Just make sure you are wearing what you should when it happens and you'll thank me later.