I have an '06 Street Bob. I just rode it 2000 miles from Phoenix to Edmonton Alberta Canada in 5 days. I put a quick detach windshield, saddlebags and a rear seat/rack luggage on her. It was great and very comfortable for my 6'2" body. I have forward controls on it which helped me. Still I would like 3" extended forward controls for a longer leg stretch.
Mostly I like my HD as a cruiser. I do however like to be able to hit the highway for long rides. That's why I opted for the Dyna. Buy the bike that fits your body and what you will use it for. If finances are the sticking point, buy the right bike for you USED. Less chance of losing a lot if you decide to trade her for a different model in the future.
21 inch Monaco front wheel
18 inch 180 wide Deuce rear wheel
drag bars
Cobra pipes
Kuryakin hypercharger
Custom HD mirrors, grips, pegs, signal visors and smoke lenses.