DOGPATCH- Good thread Randy. I agree that until the time comes when a cult member, or witness experiences injustices or oppression from authority figures or others on the inside - a person generally will be satisfied with the status quo of the WT society or leaders doing their thinking for them , and they won't be thinking about freedom until injustices happen to them.
That being said as Steve Hassan mentioned in his books - deep within the human spirit wants and desires to be free. I feel the authentic non-cult personality feels that way but is buried or hidden, masked as it were behind the cult personality - which wants to be dominated and told what to do or how to live. When after some time that cult personality gets jolted by life's traumatic events, deaths, injuries, accidents, injustices, hardships- many times THOSE events can serve as a catalyst for a person being primed for a change. As you advised - I do stay attentive to my JW relatives still on the inside who may be open to change if they experience life's adversities. Like you state - we just have to be alert to assisting them in those times