Simple. Have him get 2 Chase WN visa cards for 100,000 point bonus (after 1/1/15). Charge $10,000 and he will have a companion pass. Name his son as the companion. He does the all pickups of his son in TPA using the RR points for himself and the son flies free until 12/31/16. This is the cheapest.

Charge $110,00 in 2016 to earn the pass for 2017 and repeat as necessary.

He may never have to pay a dime for WN airfare again if he can charge lots of expenses.

Real question is whether he can do the pickups himself. Otherwise, he can use the points to buy award tickets for the son & ex, just going to cost more points. And if it makes more sense to use the charging towards something slightly better, like a 2% cash rebate card and just pay cash for the tickets.

Hope this helps.