With the economy, airlines, and pilot salaries much less "romantic" than in years past, what advice would you give?
I'd introduce him to some people to act as Loadmaster on flights from small dirt strips around Bogata to Miami or the Bahamas where he'll get plenty of stick time when he's not pushing the cargo out to waiting boats on the Cay Sal Bank. After a few trips, he'll be given his own plane and get $40,000 a trip per cargo run. After a few runs, he'll have enough to start investing in the cargo and eventually be able to pull in about $1MM per load. International cargo is the best paying job in flying.