In my experience much of the negative comments about those with wealth in the organisation are driven by jealousy. This applies to comments coming from both inside and outside of the organisation.
The WTS has never condemned wealth in itself or required a life of privation. Of course they are down on education, materialism and the pursuit of success in business or even a vocation but this is in the context of this being at the expense of spending time in WTS activities. If one can balance these together then the WTS loves them - we all know the prominent elders with wealth.
I have a relative who falls into this category and he has repeatedly entertained CO/DOs on his yacht, taken them flying, had them to stay at his high end property and indulged them in many other ways. Is he a hypocrite? Not overly. He spends most of his time, as it's pretty much spare, in WTS related activities. One of his kids has been in Bethel service for years and another has been a pioneer for years as well. He has his bad points but no one is perfect.
There are those who have skeletons in the closet, those who get passes on their kids' bad behaviour due to their position, those who upset others in business and so on. I have to say however I think this applies to many, it's not just rich elders who get to play the system - there are plenty of less wealthy elders who lord it over others and get to sweep things under the carpet.
As I say, I think many comments are simply down to the little green monster.