Dont waste your money on a Heritage classic ,,,spend a little extra and get a RoadKing or a big bagger.....Heritage is a nice bike but its just a step up from a Softail and you will like the Hard bags of a RoadKing or Bigger bagger ,.
And get both , A bike and a boat....If you have both than you go to all the Biker Ralleys and then hit up Party cove on the lake for some beer and boobies in the heat of the summer...
Also if your going to take a step towards a Harley make sure you get a new enough bike it has the new twin cam engine and not the old Evo engine ....Evo' engine are and were fantastic but the reliability of the Twin Cam engine is beyond the realm of Harley.