If the guy wants to do it then yes I think you should encourage him. Project your mind back 30 years, I am sure there were older guys giving it the, "its not the same as it used to be" Did it stop you, obviously not.
I am not surprised that the family are not keen on you discouraging it, most people when they were wannbies would have loved to have someone in "the know".
Fair enough tell him about the pitfalls then he can make his own mind up.
There are a lot worse ways to make a living, and in this day and age, aviation is no more volatile than a lot of jobs.