I have been giving this subject some thought recently because of parents becoming old and possibly donating money to the WT.
Because my mother grew up poor, she is a penny pincher. I would like the buying of property in New York (more expensive than in other places) and the selling of the properties for millions - to get her thinking that they have more than enough money and don't need hers. But as Drearyweather said, they see it as a positive. I tried it on a "friend" and that was their response.
For me, a much more simple illustration in the here and now for my mom, showing the hypocrisy is - the poor little old sister who has very little in her fridge and is encouraged to drop everything she has in the contribution box. (picture and story in the Wt) And then say, "and yet, when you see the GB on the screen, most of them are obese. Are they missing any meals or going hungry? No they aren't. They are eating from what that starving poor sister put in."
That is the theme of the WT. I wish I could remember what study article it was or book, but some "leader" encouraged the bros and sisters to make sure they eat a sandwich while out peddling books. It was supposed to show how much they "loved and considered" the other sheep. But in reality, there was Beth Sarim. Millions of dollars in real estate and free labor - brothers and sisters tortured in mallawi and no help from the WT. Warwick - brothers and sisters keep your lives simple. The list goes on....