Thanks to the winter lesson program we moved my lessons to a different barn (and a lesson horse with smaller movement). Sitting the trot on that guy was a BREEZE! Easier than posting, really.
He's got the lazy lesson horse thing going, and decided that a lope-like canter would be easier than the collected trot I wanted him to do, so he kept attempting to break into the canter instead of collecting the trot. Eventually, we decided to just go for it with the canter itself, I learnt the cue, asked him, and we were off! Trainer said it was a much slower canter than I should expect from my boy once he's back in trim come the spring, but still! It was a proper canter, and it was easy as pie! Both ways - going up, and coming back down, smooth as glass! Yay!