Here's what I would do Dave:
I would take MB up on his offer to play with you, but.....not in match play. It would be much more rewarding for you to achieve the legend by earning it not having him give it to you.
However, if he is willing to play a few matchplays to do that, maybe he would be willing to play a stroke play or two with you and who knows maybe he could teach you something. It was a TL that did that for me. I am not elite, but certainly decent at legend and getting better and it was because a TL took some time with me and helped me.
Its obvious, that if you are having those challenges mid round or whatever, and your stats are showing these guys som ethings, thatyou are missing a few small things, some slight nuances and maybe MB could help you overcome them