I prefer the 250 over the 500. The $2000 price differential to me doesn't justify the additional 20hp at the expense of a full fairing. I'd rather buy a used 250 and spend a few hundred dollars on suspension upgrades to it and turn it into a first-rate road bike. The money you save on insurance and bike costs more than make up for it. Both bikes can hit triple digits and the 250R is just more fun to ride as a single rider.