I used to run a wilderness camp that featured horseback riding, wilderness pack trips, etc. as it's program. It is in Southern Alberta's cow country. And there I ran into two kinds of attitudes among the cowboys (the real ones that is). There were those who set a great deal of stock in their own "steet cred" and looked down their noses at anyone who they saw as an interloper. Sniff at their horses, their cheap mass produced saddles, their hats, their boots, their chaps ... you get the idea. Then there were those who accepted you as you came to them, and were grateful to find someone from outside of their circles who was interested in learning, and preserving cowboy skills. They would teach you about what made a good saddle good, without calling yours crap.
I knew an old saddle maker who often got asked to fix people's store bought rigs. He did so without criticizing their purchase. He would put on the coffee while he worked on their saddle, and just visit, and subtly teach. As a result of his approach, he sold a lot of his handmade, beautiful, tough, and functional works of art to these people. One of my biggest regrets is that I didn't beg, borrow or steal the money to get him to build me one before the cancer got him. Anyway, I learned a lot from him. And I learned a lot from those who sniffed at my gear when I first started out.