Wanted to update that the new bridle (well a combo of different pieces from a cob / horse bridle to fit his funny big little head) and a new bit have made a world of difference.
I’m using a Myler Level Two Loose Ring and he plays a little with the part in the middle but in a happy way. No tongue issues, much better feel - easier to get him relaxed it seems and reaching without bracing / grabbing against me. Our flying changes have been way better too and I think it’s the improved contact.
The D-ring mentioned up thread I also tried and he HATED it. Like, almost as if it were poison. He was having such a fit about it I had to take off the bridle and lead him back to the stable with the reins around the neck only. I have learned he has real opinions about his bits I guess?