At 285 lbs. I would suggest getting the Vee but I am sure the Wee would be plenty enough for you also.
1. Vee more power but less mpg and a few adjustments usually needed
2. Wee enough power and better mpg ready to ride out of box (from what I have heard)
That being said, I really love my Vee and plan on keeping it and riding it for a long time! My next bike will also be a Vee but newer.
2004 Silver V-Strom 1000 & 1994 Yamaha XT600
Farkles? Sargent Seat, Genmar risers, K&N filter, cramp buster, heated grips, PCIII, Givi Engine Guards, Givi Hard Bags 52 liter and two 45 liter, Givi shield with spacers for buffeting.