RE: Having trouble asking permission to hunt.
All of the suggestions sound great. I find my property through ordinary conversations. I scout areas the I want to hunt all the time. Sometimes just from the road other times just hiking around. I have a lot of potential areas to hunt. While in normal talking to people I always work in the deer being out of control and you would be amaved how many people hate the deer. They either have a problem or know someone who does. Then I point out how I can be a solution.
It's worked very well for me. I have many more places to hunt then I can get out. I choose the best spots and also work in new places. I'm currently trying to gain access to some property in Alabama, just because I've never hunted there.
Good luck and never be afraid to ask.