Desert Dude,
Whirly-whatever-her-name-is hasn't really got the helicopter flying experience to comment, but since you mentioned my name - well, nearly anyway
I guess it just depends what you want out of life. I've done all sorts of different things, and yes, I've been called an under achiever too, just because I never followed a conventional career path or made lots of money. But I did whatever I wanted to do when I wanted to do it, and that kind of freedom is what's important to me. If the rest of the world disapproves, that's their problem not mine.
Five years ago I inherited some money and decided to learn to fly; two years later I discovered helicopters. I keep saying I wish I'd started flying them years ago, but if I had, maybe I'd be as disillusioned as some of you are now. As it is, maybe I can actually get paid to fly them someday, because otherwise I won't be able to afford to. That's about the sum total of my ambitions, flying-wise, right at this moment. If that makes me an under achiever, so be it. It's what I want to do right now. It may not work out, but life is a dangerous and unpredictable business.
When I was considering spending huge amounts of money on a CPL(H), a man in his 70s told me to go for it. "You never regret what you have done, only what you haven't", he told me. I always remember that. I don't intend to end up looking back and saying: "if only..." I'll know at least I tried.