Just my opinions of course;
Money:
A common attitude among ex-JW's is that the Watchtower will face collapse only when the money dries up - I disagree. Even if impoverished, taxed and stripped of charitable status, the WT would continue to command the loyalty of millions of followers, those trials might actually increase the loyalty of the rank and file.
It's the perceived AUTHORITY of the Society that needs to weaken, not its finances.
Doctrine:
Again, it's often reasoned that losing the 607 B.C.E date for the destruction of Jerusalem would end in disaster for the Society. Sorry but I just don't think so. The Society could adopt the 587/6 date and 95% of dubs wouldn't even think twice about it. Why? Because they perceive the Watchtower to be teaching with AUTHORITY.
AUTHORITY is the key. The society can change or drop any teaching or date it likes; 1914, 607, the generation, the anointed, the remnant, anything! There are no sacred cows except one - AUTHORITY. They can dress that authority anyway they like and attach a new name or label to it, they don't care so long as they retain it.
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A lot of good people have spent years of their lives researching the Society's doctrines and finances and thousands of us have been freed as a result - I thank you all! But doctrinal essays and the exposure of U.N. type cover-ups or pedophile abuse will never result in a mass exodus of affronted and shocked JW's. Some will murmur, a few may leave, then they'll all pick up their Songbooks and sing like before . .
We need creative thinking on undermining the Watchtower Society's perceived AUTHORITY!
Nic'