The Chinese have a saying which means "Wealth never survives three generations." Similar meaning phrase exist in other cultures as well, such s the Italian saying "from the cowshed to the stars and back to the cowshed."
Inheriting wealth, or position, does not mean you created wealth or earned your position.
I believe Watchtower and JW's are currently, more or less, in their third generation of leaders, with a little overlap between each.
1st generation - Russell / Rutherford
2nd generation - Knorr / Franz / Henschel
3rd generation - current governing body
Changes to Watchtower eschatology that started in the mid 90's after the death of Franz, such as the "generation" teaching and "sheep / goats" teaching were simply a band-aid approach to maintain power against the back drop of failing predictions.
The year 2000 saw big changes after the death of Henschel. A great focus on lawyers and wealth creation became more important that eschatology. Watchtower was divided up and the flood gates were open which resulted in the creating of numerous legal entities that no one knew who was what. Everything seemed to be focused on the protection of money.
Ridiculous teachings and ideas were endorsed by the third generation of the governing body, even to the point of trying to reinvent the religion, such as with TV evangelism and trolley cart preaching. Foundation teachings of the JWs, such as the "faithful and discreet slave class" were dropped, and power was consolidated into the hands of the governing body.
The death of Ted Jaracz and former governing body member Ray Franz opened the way for even more bizarre changes and reversals of teachings, such a no 'evil slave' and the abandonment of types and anti-types. Prophetic interpretation fell to the wayside. The King of the North and King of the South were literally shelved as too were the interpretations of the prophecies in Revelation, Ezekiel, Daniel, Isaiah, and so on. To interpret a prophecy simply meant that one day that interpretation would be proven false. There is over a hundred years of Watchtower precedents to support this.
Every generation, and overlapping generation (no pun intended) of governing body / Watchtower leaders have traditionally reinterpreted bible scriptures and prophecy in such a way that it always pointed to themselves as the guardians of doctrine and cleansers of the temple.
The current governing body and Watchtower leaders are, not only incompetent, but are in crisis. It's quite possible the events of 9/11, which they got to witness from their offices across the East River, greatly affect them. So close to home.
Whether or not Watchtower is in financial crisis is not worth speculating beyond the fact they they are selling off their assets around the world, draining congregation funds, and cutting back their overheads on an unprecedented scale. Which ever way the governing body spin this it is never convincing. Their body language speaks more than their words.
In the past the Watchtower mantra was "Advertise, Advertise, Advertise, the King and his Kingdom." Now the mantra in "Donate, Donate, Donate, to the King and his Kingdom."
In 2000 Watchtower started creating a plethora of legal entities all of which appear to have one purpose - protecting money. The bible teaches that "shrewd is the one that sees the calamity and proceeds to protect himself." In 2000 Watchtower saw the calamity, the 'writing on the wall' and started to protect itself. The calamity is now here.
This current generation of governing body members and Watchtower leaders are the third generation of leaders. They inherited the wealth and the teachings (of hope and the last days) that created the wealth. Then they go and dump the very teachings that created the wealth. The net result is they are crying poor, and they probably really are.
I read an article many years ago about the car manufacturer Ferrari. At the time the company admitted that it could not survive as a motor vehicle manufacturer without the sponsors and royalties it derived from merchandise sales that it generated through its Formula 1 racing team. This was its bread and butter that allowed for the cream - the street cars. Ferrari would never kill off its F1 team to save money.
Watchtower have in effect cut off their income stream - hope for the future and genuine christian love. This has created a vacuum which is now filled with no hope, no future, no good news and no financial security.
I would put 2000 as the stat of the "last days" for Watchtower and the governing body.