Idk why but I loooooooooooooove him, great expressive face, looks like he has a huge heart, awesome size! But I would do confo shots to show my trainer, I would do a complete vet check, and get a chiro out to check him for any ouchies the vet might miss.
I was told the same thing your nana told you about the tail swishing thing, intense concentration/having a blast!
Better be safe then sorry though and get him properly checked out
As to the flying lead changes and other wee issues, might be he doesn't completely respect his rider and is used to doing what he wants, might need a firmer hand in the arena. Good luck