Hey Inkling !
Very well written! Unfortunately, as the Bable says, you'd be "casting pearls before dogs returning to the mire..." or something like that. Have you tried bring up the pedophile cases? Print them out. Give them to him. Ask him how you're supposed to 'witless' to someone if they shove these in your face? There's nothing in the Reasoning book on why Jehovah's Witnesses protect criminal child sex abusers from police, courts, and secular justice.
I've found that bringing up doctrinal issues causes instant defensiveness and total deafness. However, whenever the published cases of JW protected pedophiles is put in front of them, they can't attack you, you didn't write it. They can't attack the writer, because it's true. Even the most entrenched JW goes into psycho fake babble mode. When they pause, as if they've made a point, just ask, "Is that the official FDS explanation, or are you speculating on this?"
Anyway, that's worked for me.