Of course this is free advice so it may be worth only what you're paying for it. You may want to take a little time and ask yourself what you'll be doing with the bake. If you'll be a solo rider and only riding around town then any harley will do. If you'll have the occasional passenger and doing some miles here and there on the interstate you'll be better off with the dyna or softail with a bigger pillion pad or any electra glide. If you want to spend the day riding to another state and will often have a passenger you can't beat the electra glide. If you passenger isn't too picky the heritage will do well too.
I like the electra glides because I like longer rides, often have my wife with me and I like the better handling compared to the other bigger harleys. Around town cornering and in parking lot/gas pump type environments the elctra glide handles very well.
Truth be told, if I ever move away from the longer rides I'll likely drop down to the heritage.
I like the looks and style of the Heritage. As far as trips, I've never done a real road trip. I think i'd like to try a ride to Florida to see my daughter. Other than that, just inside the state.