Last time I took my bags off for cleaning I thought about leaving them off, but the air shocks are so damn fugly sitting out there that I put the bags back on. Maybe if I switched over to Progressive shocks I'd think about it.
There is a reason for owning a 'Bagger', it has saddle bags on it. You want a Softail Classic buy one for a second bike.
Personally with the muffler supports for my baggers on the bag support frames there would be no way I would run it on the street without, then to make mods to make it look right I would be back to a Softail again and a lot of time spent that I would have to reverse later.