JW rogue, sympathy bro! I know others in your situation. One thing you are probably driven to is to live inside your head as it were, to think about reality outside of the JW delusion and enjoy the real world that way. To physically leave suddenly of could make matters worse.
Perhaps in your casual comments you could stress the facts that the early Christian congregation seemed to think that welfare within the community was a priority (widows and orphans), The GB couldn't care a fig about the welfare of their followers even for the suffering of victims of sexual abuse. In fact the more they suffer the more dependent they become...
JWs I think, might be likened to a troupe of high-wire artists who have all fallen into the safety net...that is the KH community. from their viewpoint there is nothing underneath the net left to save them. It is this crippling vision of their place in life which holds them there in fear.
People who believe they are worthless will punish themselves and make bad choices.
The Watchtower of course encourages this since fear and worthlessness are the very factors they routinely exploit. The only people useful to the organisation are those who are guilt ridden, emotionally and educationally stifled and who therefore remain totally dependent on it to give them the imaginary fix of paradise .
Suggestion 1
Have you thought about building up your wife's self confidence as opposed to her abject religious dependency? A new job or new interest?
Suggestion 2
How about continuing to take it slowly, keep them on your side but sharing things you have learned which get the family to start thinking for themselves? Make some allies in your mild scepticism, preferably including your wife.
Suggestions 3
Expressing the oddness that if Big J was behind the JW org, surely, you would have thought he would get his dates right? The WT teaching for seventy odd years that the generation which saw 1914 would also see the end? JWs have never got a prophecy right...nor did Jesus get his generation prophecy right. Mark 9,1.
It's a trap all right!