First the grey pony. By the pictures you have posted up, he looks like a classic when he is set up, but the movement could go modern pleasure. But you said the picture was taken while he was playing. Most ponies trot higher while playing than when they are being worked down the rail. As for the diference between classic or modern pleasure, I like to see more of a head set and movement on a modern pleasure than on a classic. I like modern pleasures to trot level or a tick above with some extension. A classic should be below level, less knee bend and with extension. Both classics and modern pleasures line up the about the same and both work off the rail. Classics and modern pleasures are alowed tailers just as moderns are. Classics are alowed to be shod but can only have a light plate without pads, toe clips, side clips or heal caulks. Modern pleasures are alowed a light shoe of even weight, a light pad, toe clips and side clips.
So, what it all comes down to is, where do you want to show your pony?