That's an interesting point about there being badness during the thousand years on the basis of John 5:29. They don't show that in the pictures.
Are you a Bible believing Christian still? I'm not sure I'd want to use the Bible in a discussion in a way that indicated I believe it has authority. But I see the angle of defending the Watchtower position against the JW, and the irony of him taking the wrong side.
I mostly pass JWs at carts by these days. I am at a loss to know what I can tell them that would do any good. JWs who are full in are apt to turn any sort of conversation you have with them into evidence that their religion is true.
If you present as a member of the public with a question it confirms their identity as a person who answers the truth from the Bible.
If you catch them out in some way then you may be labelled an opposer or apostate, in which case this is further proof that they gave the true religion because, persecution!
JWs have been so well prepared mentally to fit any sort of interaction with anyone into a narrative that confirms that they have the truth that it's virtually impregnable.
I am convinced that JWs rarely if ever are dissuaded from believing the religion on the basis of rational argument.