I've been riding my 250R for a couple of years now. It is my first bike. I ride my dad's Road Star (1600cc Yamaha cruiser) quite a bit too. I like the ease of handling the 250 and I'm a careful rider, but I frankly get tired of shifting so much to get going and to get around in traffic, and I'm not a big guy at all. I also find the seat pretty uncomfortable for longer hauls, though I have changed the grips and they feel great now. Of course, the Road Star is very comfortable because of it's size, but it is a lot of work in the stop and go stuff. I'm afraid the 500 won't be enough of a difference in torque and weight to get me the reduced shifting and smoother and more comfortable ride I would like (at a bargain price). I bet a lot of you have made this move, and I'd really appreciate hearing how it turned out. Thanks.