Sorry, did you just say :hah:Harley??!!
Sorry, did you also say you're joining the Wild Hogs you want a Sportster???!!!
If that's how it is, you might want to give the 950 Bolt a try - All the styling of the 883, but performance comparable to the 1200, if the reviewers are being honest about it.
The Harleys would be an investment, as they hold their value... but might well eat up any future profits in the cost of parts.
Vmax - Try one out, if you can. You might like them. Lots of variety between models, it seems. I understand the imports have more kick to them. One of the guys round our way just picked one up and the specs were notably higher, on the page at least.
1100 Drag - Grown up version of the 650. Notably higher performance, but still a Dragstar. Might be even better after you mod it. Usual known issues apply.
Couple of guys round here have them as daily commuter rides.
Wildstar - Not that many about, but very well liked by their owners. Big, heavy, massively grunty torquey things. Sound great. Perhaps wouldn't mind one myself.
VN1500 - Lots of curly girly Classic styling. Change it immediately, for God's sake!!
As always, just my own thoughts. Your experience may differ.