My thoughts on the Vee vs Wee: I'd like a little more power from my 1000, so for the type of riding I do, commuting 95% freeway (or at least roads with a speed limit of 55+), the Wee wouldn't cut it powerwise (I say this learning from experience after buying my first and only new bike, a '88 Hawk GT that was a blast to ride, just not with all my friends who had bought FZR600's).
Going from there, buy whatever your budget will allow. Go newer and spend a little more $$$, or if you're undecided, get an older model for a couple grand and see how you like it. FWIW, I picked mine up for $3000 and 35K miles. It came with Two Brothers pipes, a PC, gel seat, skidplate and full Zook luggage. Sold the luggage for $500 in a day and the mods were all stuff I would've done so I think I got a pretty good deal.
False motivation is better than no motivation.