Welcome!
A very intelligent and fair first post for you. I think there is a certain danger, given the intense emotions often involved in this process of searching for answers, of responding to some in a way that seems derisive. A lot of folks have their own emotional baggage that is a result of their experiences, and it bleeds into certain topics as a result.
I think appealing to the minds and hearts of those who are genuinely troubled by or having doubts about the Witnesses or the Society is important. It was what helped me the most. I think the first site I visited was 4Jehovah.org. One of the first stories I read there touched my heart, because it described to the letter exactly how I was feeling. I had never read such personal experiences in the Watchtower; I think I always knew what to expect, and rarely were deep feelings of the ordinary Witness truly, openly discussed in the literature.
I actually had a similar thought about the Reasoning book, although my scope was intended to be much larger. I wanted to cover ever subject discussed in the Reasoning book from A to Z.
But it's true--Witnesses need to feel safe, because there is a lot of fear associated with 'apostates' for them. Presenting factual, verifiable information to them is extremely important. Even the slightest inaccuracy or distortion could cause them to conclude the Society was right after all and cease their search. Such would be their option, and for many reasons, I can understand such a choice. But I know I would never want to be responsible for causing someone to buy into the broad generalizations made about those who disagree with the Watchtower Society.
Well, I wish you the best on your path. If you ever need any help in researching some Watchtower-related matter, feel free to send me a message, eh?
--sd-7