The money question is a good one. I don't have an answer, and I don't know if anyone can make guesses at their income and expenditures that are accurate enough to be able to figure out where their money is going, and whether they might be making beaucoup bucks or even be in financial trouble. It might not seem like that is possible, but cutting down on meeting times and literature page counts is a drastic measure to take without good reason.
It's not like you create a brain washing cult without actually meaning to do so.
I'm not so sure about this. Some people have a combination of charisma and a desire for power that just kind of does the work for them. Did Hitler know psychology, or Jim Jones? They were idiot savants, in my opinion, and their area of "savantitude" was controlling people.
Certain aspects of WT teaching might seem intentionally devious, like discouragement of higher education, but I personally think that the stance on college is as simple to explain as this joke:
Patient: Doctor, it hurts when I do this.
Doctor: So don't do it!
The Society has waffled on education at times, but they've now gotten enough data to see that when kids go away to college, they frequently "fall out of the truth". So they don't want kids to go to college. The points some have made of how the higher education teaches the kids critical thinking, and how outside knowledge is dangerous to a cult, could be completely tangential to the simple possibility that the GB sees something that hurts and tells the JWs not to do it. If they are true believers then they believe that Satan is trying to mislead people with various aspects of his system. They also know the Bible verse about bad association. Thus you can entirely explain the anti-education stance even while assuming total sincerity on their part.
Just to be clear, I can't say that there is not an intentional, scheming aspect to what the Society does. There might be. I just see a plausible way that they could be sincere and still become effective at controlling people. After all, the current GB could very well be as conditioned as we are, by the previous generation of the WT leaders.
Imagine if every time you tried to go in a closet at home as a child, your parents did something frightening like shouting at you or making loud noises. You could grow up afraid of closets. One day, having become a parent, your child goes to open a closet door, and you reflexively yell at them, "Stay out of there!" When they ask you why, you can only say, "Listen to your parents, junior, closets are dangerous."
(Apologies to Christians for the rest of this post, but I'm talking to cookiemaster, who has said he's atheist.) The very existence of religion in this world is predicated on superstitions that get carried from generation to generation, isn't it? Can you believe that we actually once believed that Jesus was an angel who came to earth and healed people miraculously, and not one word of this was recorded outside the Gospels? We believed it because lots of other people believed it before us, and we figured, "There's no way they could all be wrong!"
When we went door to door, we were telling falsehoods to people, and sometimes even dissembling in order to get people to listen longer ("We're not looking to convert people, we're just here to discuss the Bible with people"...). Yet it came from a genuine place in us, didn't it? There was no intentional pyramid scheme being carried out, where we knew we had to convert x people to make back our own investment. We thought we were doing the right thing.
As I've suggested before, the Society could be viewed as a sort of organism that adapts in order to survive, just as religion is a sort of mind-virus that travels from host to host. Viruses don't care much about their hosts and organizations don't care much about their constituents. I'm willing to bet none of us have ever intentionally gotten someone sick by sneezing on them while we had a cold; but we've passed on the germs anyway.
In this case, the analogy to religion also serves as a partial explanation of what might give the Society a cult-like characteristic. The leaders (and followers!) of the org are acting to preserve not only their position in the structure, but also their belief system. After all, what does it say about the truth if the org. starts shrinking drastically before the end comes? If people come back from college asking difficult questions? For their own sake, if no one else's, the GB could discourage higher education just to stay sane.