I have an 07 Bob. Stage 1 with Rineheart 2-1, PCIII, and AN Big Sucker. Detachable, quick-release winshield and sissy bar/luggage rack. Mid-controls, so I put on highway pegs for stretching when not around side streets or lots of traffic. May go to forwards at some point. I have the HD sissy bar mounted luggage-goes on and off easy just like the other stuff.
Just did 1600 miles round trip to Asheville, NC this summer, no problems, great trip. Bike handles well 2-up or with gear and can motor with the tourers. I would reccommend to anyone, but it's my first HD. I can see adding a bagger at some point for longer tours, but the Bob is great for around town and 300-400 mile days. For longer I would want a bagger/tourer.
PM if you would like some pics of the bike in various configurations. I couldn't figure out how to put them in this message.
Hugh