Maintenance of Speedplays is stupid easy. A few drops of your favorite synthetic lube around the cleat mechanism once every month or two, and greasing the pedals once a year or so.

Clicking in is quite easy to0. Just step and click- no worry about position of the pedal or shoe, other than just being on top of the thing. I've had mine about two months, and can almost always click into them while starting to pedal away from a standng position. Very little need to look down at them or futz, though sometimes I'll just miss it, and need to correct.