Your friend seems pretty smart to me.
Back in the day, when I used to believe in God, I always believed most strongly in the reasonableness of God. I mean that my mental image of God was like a very sensible, wise, calm and compassionate Grandparent, who also had the ability to understand our motivations and feelings. I could not square this with the idea of a God who would be killing basically good people (like your friend) on the basis that they'd politely declined to speak to some jws who'd called on their door one time or another.
The whole setup seemed so deeply unfair to me. There were good, honest people that I knew who were about to be destroyed at armageddon, and the weren't really being given a chance. Put it another way, if you were God, would you save your friend? Of course you would, and so would I, and I've never even met him. It would be the sensible and reasonable thing to do, because he seems to be an alright kind of chap from what you've said.
Aahh, but what if they're right? In the end I reasoned it out this way...
Is God seriously expecting me to devote my life to a very weakly logically formulated religion, just in case they have the truth? I'm not expressing this very well, but I hope you see what I mean.
To put it another way, if armageddon happens and God says to me "you should have stayed a JW, my son. The whole crappiness of the wt logic, no evidence whatsoever for 607bce etc etc was just a giant test of your faith, and yes I am going to kill a whole load of people just because they shut the door on the jws when they called", then I am going to be extremely pissed of with Him, and justifiably so, in my opinion.
ig