KW - Here's my 0.02. If your boy is considering flying as a career, I would say this. If you are looking at the cost benefits of educating your son and enabling his aviation dreams, I would encourage him to go to the military (Navy or AF). The training is second to none and if his commercial aviation carrer is degrading at an unacceptable rate while he his 7-10 year service commitment, he would have the option of staying to his 20 year retirement. Additionally, the experiences, friends and maturity gained as a military aviator are without equal.
Secondly, I would encourage you to be financially smart and also to retire at 60 or earlier. If you are here asking how the civilian aviation landscape will be for your son or some of your fellow pilots' children, you must consider how your actions effect you son's dreams. SWA and other top tier jobs are very hard to attain. I do think there is a slow degradation of these top tier jobs. By staying 5 more years only hurts his chances by that much. Contrary to popular belief, there is not a pilot shortage. There is only a shortage in jobs that pay unlivable wages. Imagine your son's road trying to pay back college loans, buy house, start a family, ensuring decent medical coverage on some of the regional wages. Our children's QOL is going to be less than ours, it is only a matter of how much.
Spartan
ps. An added plug for the military is that your meical is paid 100%. Check out military pay rates for O-1/2/3.