I’d be interested to know what makes the earlier bike your preference? That late model sure is a beauty.
On a somewhat related note, I just saw today where LaMonster is auctioning off his late model Rocket 3 for a charity. When I saw the post the high bid was a little over $5 grand, so there is still time!!!
The ergonomics of the 1st gen are a bit more comfortable to me, and I've changed it further by replacing the OEM bars with T-bars. The second gen has the traditional style of handlebar that is just a bit awkward and T-Rex-like for me, and this is unlikely to change, given that replacing a system with fly-by-wire inside the handlebars sounds utterly unappealing.
I also appreciate the analog instruments of the 1st gen. Fewer electronics, less crap to worry about. It also has a traditional throttle-cable system, rather than fly-by-wire. The second gen has a full on TFT display with traction control, multiple ride modes, hill assist, etc., but I'm old school and hardly use any of that stuff. That said, the quickshifter is excellent and stupid-fun to use.
Finally, the look of the 1st gen (especially in that particular color scheme) is just beautiful (to me). It perfectly combines tradition and legacy with hints of anarchy. The second gen is beautiful in its own right, but more in a "Marty-McFly-went-to-the-future-and-brought-back-some-Mad-Max-inspired-equipment" type of way.
In spite of my own bias, the 2nd gen is the better motorcycle: it is significantly lighter, more powerful, and smoother. Both bikes will smoke just about any cruiser out there, and it takes a fair amount of testicular fortitude to yank the throttle wide open on either platform.
Those look like great bikes.

I see them around here from time to time.
But I need some bags for gear and stuff. I try to avoid the rain and cold these days, but not always.
I hear ya. For me, Rockets (of either generation) aren't really sensible long-distance bikes. I can do a few hundred miles per day on them, but they wouldn't be my pick for consecutive 500+ mile days. The Valkyries are solid bikes that will do most things pretty well and are definitely my pick for twisties (Standard) or long-distance hauls (Interstate).
That said, you can get luggage & windscreens for either generation of Rocket.