Eh, I have a decent record, no major accidents. It was going to be $110 the first year but when they found my speeding ticket (only 1) it jumped to $130 for the year (woopie) but the second year it came back down. To be honest you may be fine with a 250 but I would still recommend the 500, it has the benefit of being a small bike (two cylinder carbureted) so it's very forgiving to learn on but once you get some skill it still has enough power to keep you from outgrowing it too fast. To be honest you will probably never outgrow a bike skill-wise, only speed-wise. Meaning, you will probably never be able to push a bike to it's riding limits because if you could then you would be cleaning up on the race circuit, what will happen is you will get used to the acceleration/speed and want more of that. However, if you're a responsible rider that doesn't care about going over 100mph the 500 might keep you interested longer than you think...