Hmm I don't think age guarantees wisdom either. I don't think simply because someone is older than you, that they automatically know best. I do think they've lived more than us though and what you might see as settling for less might have a different explanation in their own minds, might make more sense.
It's easy to judge someone, especially when you haven't been in their shoes, you know? I think people make the best choices and decisions they're capable of making at the time. :) Very interesting idea :)