I bought both last year when we started to ride. I have the 650 and my wife has the 250. The 250 is just not enough power for two people. Period. Experienced or not. My wife outgrew the 250 real fast and wants the 650. I am ready for something bigger as well.
The weight of the 650 is really not an encumbrance. I found the bike very stable and easy to maneuver. The seat is at 28″, fairly low clearance. If you want, you can add a get seat that will lower it another 1-2 inches. You can easily lower it more if you want.
If I had to do it all over again today, I would buy the 650 for the wife and something a little bigger for me (maybe the Vulcan 900 or a Sporster.)
I don’t know where you live but I know in the LA area, used Vstar 650 got for around $3500 (that’s for an 05-07 with 3-5K miles on it.) Your buddy’s bike oughta be pristine for 4k.
