Good luck, doogie. It is hard to talk to JWs that are still convinced it is "the truth." Usually, something has to happen to them, some unloving treatment by the congregation towards them or someone close to them, to make them wake up. Lying and deception by the elders or elders wives might be a start.
Mine was over the child sexual abuse issue and how the WTS handled it. I did not not need Silentlambs because I had seen how it was handled in the circuit over a 40 year period. Nothing ever changed.
As to prophecy, as I read the WTS older publications, I found these 2 points interesting and illuminating.
1) That until 1943, the WTS had taught that Jesus' presence started in 1874 not 1914. (With a little research, this can be found on the WT-CD; use 1874 as a search word)
2) That the WTS had taught that the end was coming in 1925 and that Abraham, David, Abel, etc., were to be resurrected and rule over the earth in Jerusalem.
This was in the Millions Will Never Die publication
A simple calculation of these jubilees brings us to this important fact: Seventy jubilees of fifty years each would be a total of 3500 years. That period of time beginning 1575 before A. D. 1 of necessity would end in the fall of the year 1925, at which time the type ends and the great antitype must begin. What, then, should we expect to take place? In the type there must be a full restoration; therefore the great antitype must mark the beginning of restoration of all things. The chief thing to be restored is the human race to life; and since other Scriptures definitely fix the fact that there will be a resurrection of Abraham, Isaac, Jacob and other faithful ones of old, and that these will have the first favor, we may expect 1925 to witness the return of these faithful men of Israel from the condition of death, being resurrected and fully restored to perfect humanity and made the visible, legal representatives of the new order of things on earth.
Messiah's kingdom once established, Jesus and his glorified church constituting the great Messiah, shall minister the blessings to the people they have so long desired and hoped for and prayed might come.
Based upon the argument heretofore set forth, then, that the old order of things, the old world, is ending and is therefore passing away, and that the new order is coming in, and that 1925 shall mark the resurrection of the faithful worthies of old and the beginning of reconstruction, it is reasonable to conclude that millions of people now on the earth will be still on the earth in 1925. Then, based upon the promises set forth in the divine Word, we must reach the positive and indisputable conclusion that millions now living will never die.
As we have heretofore stated, the great jubilee cycle is due to begin in 1925. At that time the earthly phase of the kingdom shall be recognized. The Apostle Paul in the eleventh chapter of Hebrews names a long list of faithful men who died before the crucifixion of the Lord and before the beginning of the selection of the church. These can never be a part of the heavenly class; they had no heavenly hopes; but God has in store something good for them. They are to be resurrected as perfect men and constitute the princes or rulers in the earth, according to his promise. (Psalm 45:16; Isaiah 32:1; Matthew 8:11) Therefore we may confidently expect that 1925 will mark the return of Abraham, Isaac, Jacob and the faithful prophets of old, particularly those named by the Apostle in Hebrews chapter eleven, to the condition of human perfection.