So the trainer I wanted to work with came out this week and this is the result!
We’re practicing daily, but not a bad result for having a pro work with him for about an hour and a half…We’re going to let him ride loose and backwards so I think that should alleviate some of his stresses and insecurities. He doesn’t like being tied and tying just seems to make everything worse.
Three Chestnuts 
Aw yay, good pony!! I worked with a pro to get my mare consistently loading too and it was seriously so worth the investment
So happy with him! He’s been great practicing and hopefully it’ll continue.