Great topic. I was born in a little harbor town in Holland, a 4th generation witness. Grandfather and father were both elders, I was MS+, doing the public lecture at sunday morning.
What made me wake up?
1) my family were no die hard JW's. Because generations before me were "in the truth" we knew and did discuss about topics like 1975, Russell, Rutherford and 607. At the end the discussion was closed with "ok, this is wrong, but we are the only organization using God's name and doing a world wide preaching, so the rest has happened but is not a focus point".
2) from my early days, during the congregation meetings, I had some feeling that "something was strange", when it became the discussed literature. At the Watchtower study I was reading the magazine and it caused pain in my head.
3) when I was 9 years old, I drove with my father to the secretary's house, we had to hand over our monthly reports, late again as ever. I stayed in the car. And waited 5 minutes, 10 minutes, 30 minutes and when a hour went over, my father came back. I asked "where did you stay?" he explained that the secretary showed the current Time magazine with an article about Raymond Franz and the organization problems.
4) at the same time in 1980 I was preaching with my father (my all time hero!) and the householder told us "You both lovely people are preaching here at sunday in this extreme cold wintertime weather. Do you know your religion leaders are living in great luxury buildings, have big cars with own drivers, do have own planes? I have seen it all living in the USA, it's all about making profit. You are being used!". My father did some defense, but I never forgot the householders remarks.
5) my JW best friend (studying at University) told me his reverse opinion about the organization when the 1995 generation change occurred. Before that he made sometimes remarks about the organization. It influenced me, and I felt he could be right. Later on the gave me Ray Franz's two books.
6) The books of Ray made me feeling disgusting about the organization. Once read, I could never believe again in my religion.
7) All the information on Internet made me proof most of the witness policy and doctrines are worthless and focused on the interests of the organization only. I read it all, starting on the old Hourglass, then of course the highly valuable jehovah-witness.com and Cedars made some very good points all.
8) Highlights: Ray Franz publications, the declaration of facts written by Rutherford to the Reichsfuhrer of Nazi Germany in 1933, Beth Sarim, the 1874 and 1914 mistake, the closing of the calling, the generation change, the change about voting (you can vote now!), all the financial matters, like using your credit card for donation, and the current generation change with Frederic William Franz for the turning point and of course the change to Television / Broadcasting religion.
Preaching on a cold winter day in 2007 I walked with my lovely wife in a small village noticing that all people were watching us but didn't open the doors. I told my wife, this is my last day in field service. We never went again. The same with attending the meetings. In 2012, after attending, I told my wife, this is the last time I attend a meeting. She agreed with it and now we are only attending memorial to keep the close family satisfied.
Pfff. Gorby