Joseph,
Would you ask a strong able bodied person how content he would be if he found himself sickly and weak for the foreseeable future? How about a sighted person, how content he would be if he found himself losing his sight? Sure, people born that way become accustomed to their lot (as do most people as we age) but a sudden loss of one’s abilities is traumatic.
The money a person is blessed with is their strength how one uses it and how it affects ones midos is a nisayon. Like the Masilas Yesharim says, everything in this world is a nisayon, weath on one hand and poverty on the other. So you can also turn the question on it’s head and ask how content you would be if you found yourself tomorrow in the top 1%.
Also, it has been my observation that wealth does not seem to be a prerequisite for preoccupation with money and social status.