Damn bro...
Good luck with that transition!
I tried to go from my last sportbike (Duc 999) to a cruiser and failed miserably. The thrill just wasn't there.
However I did make the leap to another bike. I got into "adventure" bikes. And the bike that fed the urge and has kept me quite happy is what I have now; a Yamaha Super Tenere. This bike could get you out of the apocalypse. And it's got enough power to satisfy.
The only cruiser I rode that was satisfying was the Ducati Diavel. It still handles extremely well. The Vrod didn't do it for me. If I only cared about fast in a straight line, it would be a cool ride.
I love my Road King. Sporty yet classic. A cruiser easy to control. And cool enough for me and cushy enough for the old lady. I've had 3 of them. And mines paid for.
If you havent ridden the Duc Monster I would check that out. They are on the market used. Fast but comfortable.
I concur with this.
And now is a good time to look at the Duc Monster because they model body is shifting, as is the engine. You'll be able to get a sweet deal.
And if someone tells you that Duc's are mechanical/maintenance whores, they don't know what they're talking about. Duc stepped up their game in about 04, and they're solid.
Here's my black 999; it was an 05. Absolutely mechanically solid; and I beat the hell out of this on the track. A LOT. They're even better now.
I could not agree with Choke more. SOLID SOLID bike.