I don't see either of your hypotheticals as "insane". Of course you call a rich guy "upper class", no matter how he acts, and a poor guy not, no matter how refined his background.
Wow - that is so totally different to how we look at class in the UK. I think what I'm thinking of the class divide, you might call the old-money, new-money divide.
Sounds about right to me. I'm not sure if "old money" could be applied when the money is gone, but I wouldn't rule it out.