The "leak free" mark can be anywhere from the moment the catheter is pulled to never. Everyone is different. I will agree that a lot of guys in public claim everything is great, but in reality, it ain't so. Listen to guys at a support group, not the crew at the golf course.
I am 37 months out, and I still leak. I have to use from 1 to 3 pads in a day, with no pattern.
Instead of just the Depends pant, have him add a men's guard, and let that guard go until a little closer to wet just to get some perspective. The pant gives a backup, and the pad can be switched out easily. That was my scheme for the first 5 months, as I had great days (3 pads) and then the next, floods.
Yes, the feedback training with a physical therapist can be very useful. I worked with a PT nurse (an RN) at the hospital group where I had my surgery to improve the "quality" / effectiveness of my kegels. That marked a major improvement for me.