Be careful, lancek, the independent leagues are a tough way to go. There is tons of talent but only a few lucky ones mainstream. Your son obviously loves the game, so maybe coaching is something to try. But good luck with your decision.
Bum is correct.
I think that most people actually don't understand about the independent leagues because they don't understand how the pro system works.
Right now the Caribbean leagues (winter ball) are filled with free agents who are trying to get signed with teams. Many will because they have experience as far as AAA, some with MLB. It's difficult, so just imagine how difficult it is with no prior pro experience.
I don't mean to be negative, but realistic. My advice would be to try to continue the game other ways, perhaps coaching as Bum has suggested.
One more thing, is this about what you "feel" or how "he" feels, because you didn't indicate who really wants this. It has to be what he wants, not you.
JMO.