Hmmm, good questions. I guess the amount of money involved would be a factor. While I'm not the guy that thinks money is the root of happiness, a large sum would do wonders compared to a $5 bill.
If I could change one thing from my past... I wish I would have taken more risks, been more adventurous and cared less about failing and being rejected. It's something I'm trying to fix but it doesn't come so easily now that I've lived in my ways so long.