It's a personal choice but I can share how I decided and why.
I rode as a kid, too. Itallian mostly with a big Kawi as my last one. Now in my 50's, I started dating a girl who owned a Dyna Low-Rider. After months of pestering me to go for a ride with her, I gave in and I rode Cupcake just to shut her up. Well, . the bug bit me again and I started takin her bike to the store, . offering to run errands for her on it etc. I decided I had to get one.
But not a H/D. Hrer friends are great folks till they start talkin bikes and then they become elitist snobs. And her bike leaks oil like a sieve, vibrates uncomfortably and she paid waaay too much for it I think. Wanted american so checked out Vic's and was sold.
After reading everything I could get my hands on, cruising the M/C forums and a few test rides, it came down to the Jackpot and the Hammer. (but the Hammer really sang to me) After reading kevinx's posts about the differences in the bikes, I decided the little extra clearance and stopping power of the Hamer might come in handy some day. I'm not interested in bagging or even a windshield. (I'm going to add the superfly cowl however.) I can put everything I need for a long weekend in a small bag and strap 'er down on the rear seat. So a Hammer it is, . . for me.
Now I just have to find the right deal. One of diamond's posts made an impression on me. He said he bought his Jackpot with the idea of making some pretty extensive mods and his only regret was perhaps not looking into getting a used one. So that's what I'm looking for because I too want to make some big changes, front and back. New raked forks and a swingarm mod.
Just make a list of what it is you're looking for in the riding experience and you'll find something in the Vic line to make it happen. Best of luck!