For something to travel with I'd go for an Electra Glide or a road king for comfort and you will have plenty of room to carry anything you need to bring with you. They FXDWG is a little more sporty That's what I'm getting next.
I wouldn't worry to much about the reliability Harley breaking down a lot is a bunch of B.S. , maybe in the 70's when amf was building them. I have been driving a 89 softail for 5 years and put 90k hard miles on her. She never left me stranded.
I would not go with one of the Jessie bikes for cross county trips That would be like going cross conty in a viper or a vet.
And Evo has plenty of power if you do a little work to it.
