I have 3 bikes, and they all have Brooks saddles (67S - with springs for my sore back). I have been told that you can tell whether a Brooks will work for you fairly quickly - even on a short test ride. If it is really uncomfortable right off the bat, it is likely never going to be really comfortable when broken in. Just broken in and uncomfortable.
For me, my LBS ordered me a 67S and let me test ride. It was comfortable immediately, and with a little adjusting (front to back; and angle) it got more comfortable. I used the Proofhide on all of them.
This winter I test rode a bike with studded tires and it had a Brooks B17. It was the most uncomfortable ride I have ever had. Even factoring in that it was a man's saddle and broken in by someone else, I couldn't imagine riding more than a few miles on it. So 86, have your son test ride a few Brooks models and I think he will know pretty quickly whether it will work for him.