1- Don't get over confident in your ability to ride, the 1000 can bite and the 650 has the performance ability of bikes in the 800/1000cc bracket.
My Wee is only marginally slower than my R1150GS was (less than 0.5 of a second from 0 to 100kph/62mph)
2- Dealer luggage here in Oz. is supplied by Givi, mine have water leak and locking issues so from my experience I would say buy aftermarket (plenty of threads/feedback on this forum to help you decide what suits you best).
3- Don't know about waiting for the next model release, I bought mine in Sept.09 straight off the showroom floor.
My Wee with ABS is the best all round bike I have owned (bike #15) and does everything perfectly for my needs.
I do a 75km commute to work and back, I ride day and weekend rides, I do one or two interstate/multi state rides per year that are usually ten to fourteen days on the road.
The rides include highway, back roads, twisties, mountain and dirt roads but no serious off road/trail rides (yet :lol: ).
The Wee has less maintenance/tuning issues than the Vee and is a smoother ride (yes I did ride a Vee before buying a Wee).
With either the Wee or the Vee you will be buying a bike that will never "just sit in the garage", I bet you will ride it more than anything else you own.
Just as a guide to which one to get, the Wee out sells the Vee by something like 15 to 1, stats like that must tell you something
Enjoy whatever one you choose