I enjoyed your post, it was well written and required no patience to read. There is not much about your argument that I can pick apart. The only bits I have comments on are
1995 Watchtower used the phrase “Jehovah’s people have at times
I always took that as speaking about Jehovah's people as a whole, including the GB and boys at Bethel and never thought of it as referring to the rank & file. I'm not sure which inference was intended when it was written.
If a brother or sister before 1995 had said they belived in a figurative interpretation of “this generation” they would have been disfellowshipped, would they not?
Even as a teenager and a Ministerial Servant, I had always told other Brothers/Sisters, Elders, etc, that I didn't think it was a literal prophecy as that would have allowed the whole world to guesstimate the coming of Armageddon and it would not allow it to come as "a thief in the night." However, I was always considered as being "different" so perhaps I was viewed as a non-threat.