I say go for it and if you like it keep it up. The wheel thing would annoy me after a while...I don't even like moving lights around.
The only thing.... bag vs rack is a very individual thing. For short 2-5 mile trips a bag (IMOE) is great. But longer ones make me really like my rack and bike bag! Really, for me, it's about the locks. Those buggers are heavy in a bag after a while.