How are his finances? I've got a kid and a niece who are thinking along those lines. Given all of the shenanigans with schools these days I'm considering the possibility of hiring a CFI full time and buying or leasing a plane, with the intent of full time training until it's done. Incentivize it with a big completion bonus. Hire either an old retired CFI or a brand new one who won't have enough TT for airlines any time soon. I have enough experience to supervise the latter and do "stage checks" at key points.