Having worn my Speedmaster daily for the last 5 months, winding it every morning before I put it on is now second nature.
The display back, although nice to look at a couple of times is a bit of a waste of time. The watch should be on your wrist!
The watch has 48 hours power reserve, so you don't have to wind it everyday. I wind mine when I'm I bored, thinking and waiting for something.
The crystal back is nice, but when do you ever look at the back of the watch?