Sometimes the most aggressive personalities really do well in terms of getting permission. I once visited a friend that had just moved into a rural area of South Dakota. I was out driving around with him in the area and he was literally stopping people driving down gravel roads and asking them permission on the spot and knocking on the doors of people that he had never met. It sounded crazy to me and is something that i wouldn't do, but in the space of one morning, he got us permission to hunt over 1000 acres of prime rabbit and pheasant land scattered across several landowners.

As for me, if someone asks me nicely and they are doing it (at least supposedly) for the benefit of a kid to go hunting, I have never said no to letting someone hunt my land.