Sold the 250r. Put over 3k miles on it, including at least 500mi riding 2up. I just hated how the back end would float with two on it, I disliked how cramped I would get, and I work 24hr shifts so I could never haul all my linens and such to work on it even with saddlebags and a tailbag. I decided that sport bike was not the right choice for me, but enjoyed getting used to the feel of a bike, had a few close calls on campus with cars (and dumb pedestrians) and got to get out on the highway quite a bit, including an exit ramp experience with gravel (I can't believe I saved it still!). I've been eyeing a VTx1300 at the dealership its a 2007 with 4k miles, was going to go 1100 but there are really no great 1100s for the price I'm looking, in a cruiser style. Really just want a bike big enough to drive the 30miles to work with all my work stuff on it (saddlebags/back seat backpack), as well as be able to ride 2up on it for legitimate trips (150+ miles).
Plus the VTx1300 is only 6k and I talked him into giving me some goodies (sold the 09 250r for 3700, which seems to be an amazing amount
). I'm still deciding about the VTx, I'm sure people will have some opinions, but it is a very different move from a sport to cruiser (going from a 250 to someting like a shadow 750 felt equivalent when i rode the 750, really didn't like it with just me, not enough go).