a) First or any day available. Don't see any need to wait unless you have to. Season is gone till next yr. before you know it.
b) Things get tough around here after Nov. Get a little deeper and closer to the bedding areas and thickets. Deer around here are pressured very hard and by now anything decent will not come out into openings until well after dark. Probably applies to your area as well. We just have alot of dog runners. Good luck