He's cute, but you need more horse!! He needs to be going forward more, he's hardly tracking under himself at the trot, and he's very behind the leg at the canter. Really work on getting him to stretch out and move forward. I wouldn't be as concerned about his head set right now, I would try to work on getting him more forward, then he can start using himself better, and develop his neck and headset and really move onto the bit and round his back. Does he cross canter like that on the lunge line? A good exercise is working on the lunge with side reins, really pushing him to move forward, and strengthen his back end, so that he can canter on the correct lead in the front and back. Your seat looks pretty good, I think once you work out some of his issues, you two will look great!! I know you said his training has been a little rocky, but keep at it, it will work out!! Do you work with a trainer regularly? Weekly lessons will help you work through your issues and give you the focus you need!! He is really cute though, love his color, can't wait to see updated photos and video!!