I ASM'd an outdoor Shakespeare (Midsummer Night's Dream) last year... One of our greatest challenges was moving everything every day. Because the play was a part of a whole summer festival, we were able to leave our stage floor, back wall, and the trusses up, but all lighting, sounds, tents (except the costume tents), props, costumes, etc. had to be moved in and out every day.
To do this, we set call 15 minutes earlier than it needed to be to use the cast as a run crew at the start of the night. We had very clear jobs for each cast member (i.e. ACTOR will move prop wagon A to the Costume Tent; ACTORS B and C will assist ASM moving speakers into place; ACTORS D, E, F, and G will move portable lights into proper positions). It made the transition much smoother. The SM and I oversaw everything, and put the final touches on (raising the light bars to the right height, reconnecting all wires, etc.) and at the end of the night, we reversed everything...
Now, in certain situations, you're not allowed to ask actors to do any of this, but the point is that you need to have a very clear run sheet of EXACTLY what needs to happen before each performance, timed to when everything needs to happen.
Break legs!