Pick your own is not without problems
I think I may have a tough time balancing polyculture plantings with the logistics of a U pick operation. I don't want to have monocropped straight rows but I understand whats been said above about neighboring crops getting ruined one way or the other.
it might be more complicated, but certainly not impossible. I'm not even sure polyculture would present that many new problems. you'll encourage folks to stay on paths, you'll be extra good about signage, you'll get a feel for who needs a few extra minutes of instructions before you let them out into your gardens. I might be a bit biased, but picking in polyculture is very much more appealing to me than the alternative. with 100 acres, you'll have plenty of room to experiment to see what folks like. experimenting with long-lived tree crops is a bit risky, I suppose, but probably worthwhile.
any chance you feel like divulging your general location?