If you start with the premise that the WTS is a corporation whose main interest is self-preservation, its' decisions make a lot more sense. It's history is rooted in decisions and habits of Russell and Rutherford, not in textbook Christianity.
Q. Why would the WTS want to get rid of fence sitter? As in, why are weak ones a burden to the cong, isn't that the whole point, to shepherd the flock?
A. The WTS has a long and checquered history of expelling dissenters. It's all about maintaining power and control.
http://skepsis.no/src/popup.php?site=skepsis.no&page=utskrift&NyhetID=74 (word search "dissent")
Q. Does anyone know if the GB gets a paycheck, flies first class, how they vacation? (I said/asked a few things to my mom who is convinced they are so loving and live poorly like other Bethelites).
A. The books are closed, so we can't know for sure. In the US religious organizations don't need to publish their accounts. You might want to show your mom pictures of the development happening in Warwick. There are artist's renderings on jw.org as well. I don't think you will find overt displays of wealth as we saw with Rutherford. I think the attraction of being part of the "Governing Body" is power, not money.
http://www.sloatsburgvillage.com/2014/03/24/watchtower-presents-global-view-at-tuxedo-town-hall/
Q. Why do they not encourage higher education- like the Mormons- wouldn't wealthier flock contribute more funds, thus more income? How does it benefit the WTS to have a poor flock?
A. Someone once said the WTS is a reactive organization rather than proactive. I am sure they have statistics on how many college-educated Witnesses leave the organization. Too many. Therefore college education is "bad". Remember, the WTS is chiefly interested in continued existence. It has to just make enough. No need to be greedy. Swiftly growing organizations come with their own problems. Better to have slow and steady growth.
http://religions.pewforum.org/pdf/report-religious-landscape-study-full.pdf
"Jehovah's Witnesses have the lowest retention rate of any religious tradition."
Q. How does millions of hours knocking on doors benefit them? hardly anyone places literature in my cong, the literature servant said they had to cut their monthly order by 65/70 percent Because they had so much extra Material.
A. It keeps congregation members busy so they don't have time to think about how useless their efforts are.