Good Job SORRY. I've found that things work best if I simply ask my JW family questions that I sincerely want to understand and no matter what they say... just leave it at that.
Often in the process of answering your simple questions, they see the lameness of their answers and they begin looking at their beliefs in a literal way and you come off as someone who is wanting to understand "the truth" better.
You: Have you ever wondered why Jehovah needed the Israelites to have an army when sometimes he used angels to wipe out his enemies?
Them: Well Jehovah always has his reasons.
You: Yeah... I know but I wonder if any Israelites were killed or injured in any of the battles? The Bible talks about them having won these battles but surely some of the Israelites must have gotten killed or injured.
Them: Well if any were killed they'll be resurrected in the new system.
You: Yeah that's true....I'll bet they're going to be surprised to find out that the resurrection happen 2 thousand years later or maybe more if it doesn't come in our lifetime. I wonder if they thought the new system would arrive in their own lifetime like we do.
Just leave it at that and let them say whatever they want. Tthe next time ask them something simple like:
You: So when the Angel was posted at the entrance of the garden of Eden, he had a spinning sword that kept Adam and Eve away. I wonder what it was made of since steel and even the sword itself hadn't been invented yet?
Them: Well Jehovah's intellect and ability to create is far beyond mans.
You: True....I suppose you could say Jehovah was the inventor of the first weapon.
Anyway you get the idea, just get them to think beyond what they've always thought about, but don't argue with them or contradict them. JW's are used to the comfort of thinking they have all the answers and they have it made. Don't be confrontational....help them save face while they sort out this new way of looking at things, that you are presenting to them.