Thanks for all the tips. I agree Anabel, ride what I have - but the comments coming all of a sudden make me think something is up with him. The vet is scheduled to come out for my yearling's boosters this first week of May, so I'm going to talk to her then.
Here is a video of our ride today. We ran through Training 3 at the end. It's rough (read: I'm ALL OVER the place) because it's just in my backyard and we don't have letters yet. Sorry the video is crappy - my camera is dead so my mom took it on hers (and she doesn't realize you can zoom, haha). But the white polos make it easier to see what his legs are doing.
Also - please pardon the spooks in the middle... couldn't figure out what caused them ;)
Looking at the video - I don't think he looks all that bad. I see where his trot gets shorter sometimes, other times it looks alright. His free walk was rough - I was pushing too much and making him jig :/