M2P each little snippet of info you give about your dearly beloved confirms my feeling that he's a dreamer, not a do-er! Sounds to me like he needs a rocket up his arse, and I guess that's what you're trying to do. Unless he gets off his tush and starts flying, aviation as a profession will never be anything but a dream. Writing letters doesn't get people a job if they don't qualify in the first place, as I'm sure you appreciate.
Good luck!
Scroggs