Hi, I'm a native speaker from the UK...I think 'good money' is fairly commonly used to mean 'a lot of money', e.g. 'you can earn good money working as a teacher'.
However the other 3 obviously have literal meanings but aren't commonly used phrases with any meaning as far as I know!
I've just googled 'seeing the elephant' and apparently this is an American expression meaning 'gaining experience of the world at a significant cost'. However I'm not sure if it's commonly used in the US or if it may be old fashioned...