I was one of those commuter guys in a prior life. That is after I had flown single pilot night freight in all sorts of wx and instructed for years. I was young, it was twin time (remember that) and fun. I had the pleasure of many a 10 leg day in a Jetstream 32. We didn't even have RJs back in the 90s but then nobody besides Comair did. I'd say 10 years is a realistic time frame. That is after you've gotten all of your ratings and landed a job that is if we're (FedEx) hiring. If you're his friend you should put him on the clue bus. If he's like the rest of us were he won't listen anyway but at least you tried. And yes, the success rate is pretty high once you've gotten the interview. As the gentleman who met us the morning of my interview said, "Welcome, try to relax, the job is yours to lose."