This is such a hard question to answer in a way that will make sense to anybody else because everybody has different values. Our goal in raising a son we'll be proud of does not have his financial success at the top of the list. Money management is certainly a visible measure of what we tend to think of as mature judgement and responsibility but it doesn't tell the whole story.
Speaking in generalities, we want our child to develop into a person who is capable of executing the decisions he makes and living with the consequences of them (both financially and otherwise) independently, and that he will make those decisions with the best interest of everyone potentially involved in mind, not just himself. That doesn't mean that we or others would never offer help (and love and moral support is a given), but if he fails we will not rush to the rescue nor should he ever put a plan in place expecting that. We want his character to be measured by more than just money and for him to be honest in his dealings, not consumed with acquiring things or status, community-minded and sensitive to the needs of others around him and generous with what he has even if it means sacrifice. We've tried to model all these qualities and are now, at his age of 18, trying to transition him away from the sense of entitlement that I think comes naturally during childhood in our (relatively) affluent society.
To your questions in specific:
If you're rich and you kids get the college paid for does that translate into an "irresponsible" "coddle" adult?
Not necessarily. Many parents, even those that are not rich, have planned to finance their kid's college. Perhaps it's been understood the child's whole live and as such, having to provide this for themselves is something that they can't even imagine doing. If those circumstances lead to the child failing to value the opportunity and waste the time and resources because they don't have any "skin in the game", then yes - that's irresponsible.
If you can't help your kid at all financially, does that mean they go to the head of the class in the "responsibility"
Not sure if it will make them all successful at it but it definitely results in a higher level of self-sufficiency.
If I have a mortgage but go buy myself $700 Jimmy choo's am I a wreck?
Not to me. Personally I can't fathom being completely debt-free (ie: without a mortgage) and I don't imagine 99.9% of the population are there either. Life needs to go on in a way that balances lifestyle enhancements with fulfilling your obligations (although I can say that if $700 would retire my mortgage I'd do that instead of buying shoes 
).
If I don't save for retirement but give a bunch of money and time to charity, does that make me stupid or a saint?
Generosity is a very high value of ours. We would greatly respect someone that impoverished themselves in sacrificial giving as long as they were prepared to live in the extremely modest circumstances that are the result. We know people who are in this position and have waaaay higher esteem for them than we do for those who are extremely prosperous and don't believe in giving.
Is it age dependent or action dependent?
Sooner or later it has to become a matter of age. For example, our DS will be finished college and have every possible opportunity to do what he needs to do to be independent by age 25. Unless the circumstances are extremely extenuating, we expect him to to be out of our home and on his own by then.
