Just my opinion, his goal should be to become a lifer at a major airline not a regional airline, I mean why aim so low, its the same job. He should choose the regional that will have the shortest upgrade time, possibly one with the smallest fleet. You are not going to be doing him any favors by steering him towards a place that has 8 year upgrades.

Regional airlines are going to come and go, bases are going to open and close.

Really all you are doing is steering him toward the lesser of all the evils, that being Compass and Mesa and away from Republic and Envoy.