You should really take Jay "under your wing". 
oh boy, what else were gonna hear....
"gib"
Well its probably too late for Jay, no matter what I could do with him. (Don't get me wrong I am a big fan of Jay's).
But here is what I would do with his training.
Up the reps for all exercizes (12-18 reps per set, with lower weights), increase the number of sets, and decrease the number of reps per set. The guys needs to learn what a real muscle burn and pump feels like again. Also train each body part more often that he does now. (Once every 3 weeks revert to heavier core power-lifting type exercizes (squats, benches, etc)).
Work with him, especially on warm-up exercizes to really increase his range of motion and get a full range of motion stretch.
Add 2 intense aerobic sessions per week to his routine (no more just slow walking on a stepper or treadmill). There are a range of high intensity aerobic workouts he can do that don't risk injury for a guy of his size.
Start each training session with a 30 minute full body stretching, and add 2 full yoga sessions per week to increase all aspects of his flexibility.
I would also make changes to his diet and supplementation regime, but I won't get into that now...
