telling you what bike to get is like telling you what food to eat .. i don't know you and everybody has their own tastes in food and bikes. BUT, I may have been in your shoes recently. I had a Kawaski Vulcan and spent money to add a wind shield, bags (after relocating the turn signals!), back rest, Corbin seat, and luggage rack. I enjoyed it for over 25,000 miles but it was too cramped for me and my wife to ride together. So, simply to please my wife ;-) I, I mean we, chose a Heritage. It already had all the extras except a luggage rack (?) but otherwise it was set up and ready to go just like I wanted. It was the same look and style I was already used to but with more room and more comfort. FYI - I did later have to add a wider passenger seat, but otherwise we've been very happy.
Face it, buying a HD is an emotional purchase really, anyway. Might as well get the tried and true classic look!
Compared to other bikes it's like driving a dump truck, but it is comfortable and stable with plenty of power to haul 2 folks and plenty of luggage anywhere.