Anyone who knows about Calisthenics understands that progression means a whole new exercise, although it might be a slight adjustment, but it's still a new move. It is not "adding weight", it is not a numerical thing that can be kept up with in Trainerize. As it stands, it would be very difficult to keep up with multi individuals progress and making sure they had the next move when it was needed.

My suggestion is a level up system, something that does exist with certain apps like Thenics. The idea being when a goal (reps or time) is met with a certain exercise, then that move is replaced by its progression. The trainer would set up what the goal is and what the progression is, creating an automated system.