with the insurance guy I'd just start talking to him and slowly bring deer hunting into the conversation until a light clicks on in his head that I'm asking. Then again I try and make friends first or be introduced at a party (good time of year for those) by a friend. Most already have given some permission and some need a little more time to mull it over, maybe next year. A few say, we'd love having you hunt there.
Work on genuinely caring about other people and the rest will come. As a result of taking care of business first I've had people here ask their anti hunting daughter in your state for me. They not only said yes but would love to put me up. Have had offers to go out west,south,east and canada. Just make friends and most of all marry a good woman who takes your food over to everybody, even people who don't want her too.
Going to a party today that the little woman is taking food too. I'm feeling good about this party on a rural farm. Got a be several thousands of acre's being represented there and you know them farmers, best way to'm is through the wifes food.