I have been lucky in all my searches for Osage. Before my in-laws passed, they always had farms/ranches set up for me to cut some Osage whenever we visited them in Missouri. Both times I went to MO for Osage after they were gone I drove the back roads around Mt. Vernon until I saw some trees that looked good and stopped and asked if I could cut a tree. As Pat suggested, I took a couple of my bows to the door with me to show the landowners what the final product would be when I asked. The first place I asked the landowner wanted a fee, which wasn’t unreasonable, but his attitude prompted me to try elsewhere. The next three places I went permission was granted as long as I cleaned up after my self. On one of these places, I cut and stacked all the wood for use in the fireplace (I did warn them that Osage burns hot and may burn a hole in the stove) and on the other two places, I cut fence posts and made brush piles for rabbits and quail with the left over branches. In addition, even though none of the owners expected it, I made each one of them a bow from a stave taken from their property. Making them a bow was the least I could do even though they had already given me invitations to return in the future if I wanted to cut more Hedge.
If you think about it, I was extremely fortunate to have a 75% success rate when asking to cut these trees. What would you do if somebody drove up in a truck with out of state plates (Montana) and wanted to cut down some of your trees? Anyway, it doesn’t hurt to try asking, especially if you are a local. On all these places, asking worked for me as a total stranger because I mentioned my in-laws had lived in the area. One other thing I noticed, which may or may not have any correlation, was that all three of the places I got permission on were well kept ranches/farms while the one who wanted a fee was, to put it nicely, a dump.