I always liked the night train, i ride one occaisionally when i switch bikes with my friend. The softail line varies so much from end to end there is something I like about just about all of them. The heritage does stand alone though.
I started riding Harley's on a Sportster and always wanted to move up to a Road King Classic, but fell in Love with a 2006 Hertiage Softail Classic!! Awsome ride and look. Just my 2 cents
I have a '94 Heritage and I think it is the best bang for your buck. Take off the bags and the windscreen and you have the look (except the front fender) of the Fab Boy. The bags are big enough for weekend trips and the newer models have the "B" motor that is very smooth. It also has one of the lowest seat heights in the HD lineup.