4) Hmmm . . . . keep thinkin' there's gotta be a CVO Sportster sometime, maybe next year to replace the Springer. 
I think a Sportster could be done with just some performance upgrades and minor appearance items like paint and wheels for a relatively modest price increase. A full blown CVO treatment would be overkill for sure.
Why not a Sportster? Your talking about a whole group of people who may think that the "big" HD's are just that - big - or too big.
My son just bought a 08 Nightster last week (couldn't get him to wait until this week).
Being a PharmD meant it was not a cash issue - just the thought of the big bikes being too big, that and the Nightster being his first bike.
He has always admired my red bike and I'm sure if the Nightster or similar had a CVO badge and appropriate trim he would have been hooked.
For the little that is on a Sportster, a full blown CVO treatment would probably not be that much of an increase, compared to say a standard EG to a SEUC (20,000 - 36,000)