After about the 3rd question, the JW will peg you as an "apostate" (using the WT definition of the word: "Anyone critical in any sense whatsoever of the teaching of the Watchtower Organization") and shut down. If he is engaged in "public witnessing" he will walk, and if necessary, run away.
I.e., you'll never get to ask the majority of your questions.
JWs used to be trained to defend their beliefs. Now that non-JWs realize what questions to ask to expose the undefendability (is that a word?) of those beliefs, JWs have been trained, over the past 2-3 decades, to (if necessary, literally) walk away.