Oh boy! The "what should I buy" is as contentious as the oil wars . But at least based on opinion and taste, not science or fact. And as opinions are like arseholes (everyone's got one and they usually stink), here's mine.
If I were looking for a more grown up replacement for my Cabbage, I'd be looking at a Moto Guzzi California. They can be had pretty cheaply for an older model, look cool and seem pretty bomb proof. If I couldn't find one I'd look at a Triumph America or Rocket III. Only bad Triumph was those rotten TT 600 things.
I wondered for a moment why WD was drooling over a CT90
http://www.lossaengineering.com/2011/08/24/1969-honda-ct90/ct90-l-side/ (no accounting for taste) but realised my error.
I just picked up an Aprilia RSV1000 Mille but I don't think that's any help to you. If I found one for sale here, I'd buy a Ducati Indiana. Who wouldn't want a 650cc sport bike engine wrapped in an awkwardly styled cruiser chassis?
just for laughs.