I've owned Harley's since 78, during the AMF years
doh
through today. I currently own two, a 12' Ultra Limited shaved down to look like a Street Glide with more bells and whistles and an 07' Fatboy.
Without knowing your experience and physical stature it would be impossible to recommend anything. New or used? ........... I could help with most of the model twerks through the years. Unlike TR, if it's gonna be a Harley, it wouldn't be a Vrod. It would be nice until the fun wore off, it ain't fun to ride long distance and the resale is the worst of the Harleys. And the resale is one of the nice things about HD.
I've always had a Big Twin, I'm just too big a guy to be seen on a Sportster. The Big Twin starter is the Dyna (old Super Glide), it has the big motor, has plenty get up and go, and rides nice but eventually on a longer rides the vibrations become more noticeable. If you want a good all around bike that cruises but still light enough to have some jump in it's shorts it would be a Softail model. It has the hardtail look (with hidden rear suspension) and is very popular model (see the Fatboy above).
My pick has been the touring bike since 86'. I like the FLH front end (big/wide) with the larger tires for stability. There is nothing like the ride and features it offers. Heavy, smooth ride, swingarm w/shock absorber rear suspension, footboards, heal/toe shifter, saddle bags, fairing with stereo/CD/BT, cruise control, 6 gallon tank, and comfort! See pumpkin above .................