Assessment includes different aspects as in tastes, character, attitude, personality, behaviour, etc. He definitely is a Mr. Scrooge with inferior tastes like Gates, LOL!
BTW, you can be poor and yet have impeccable tastes, or you can be filthy rich and have Bill Gates' tastes--it's really either you have it OR you don't!
Taste's are subjective so too judge someone based on what you think is good taste is foolish and ignorant. If someone chooses to drive a $5k car to work because it is practical does not make them inferior but since you would consider the car poor taste you would judge them as such. I drive 02' Honda accord to work, it is great on gas, my 2010 SRT8 sits in the garage. So to you, by me driving an 02' Honda Accord, I am inferior. To others, my 02' Honda Accord is practical and they may consider me smart and practical. If I am driving my '10, some will call me flamboyant and inconsiderate of the environment. Bottom line, if you instantly judge someone based on their material things you will lose and are a poor judge of character, character which has zero to do with material possessions. Hell I give more credit to someone with a paid off 02 Honda Accord than I would to someone driving a 2012 Ferrari and up to their neck in debt. Since you are here I will assume you are a Steve Jobs worshiper. That fool wore jeans and black turtlenecks, if you did not know who he was and saw him on the street how would you judge him?