I’d be a little cautious looking at what people did more than 10 years ago. Things have changed, and will change again. The mainline airline (domestic US) for which my dad flew paid for him to get his training and paid him while he was in training. I don’t believe any of the major airlines do that any more, so it isn’t a useful strategy for a potential pilot today.
The military has even more stringent health (including vision and hearing) restrictions than does the FAA. Additionally, it is very competitive, and many aspiring pilots don’t get selected – but you’re still committed to service.
Has the OP’s son looked into opportunities (even as a teen) with the Civil Air Patrol?