I don't think you'll find a single instance where that works.  (though I'm curious if anyone knows of any)

Like, if someone is already having *very* serious doubts about the religion, they may start gradually doing research online.  Or maybe if they were a teenager and never really believed it anyway.  But to go cold turkey from active believe it all jw to even considering apostate arguments?  Never gonna happen.

It's not the beliefs themselves, but the criteria for believing that's the problem.  You'll never win any rational arguments, because they don't believe in reason to begin with.  It's better to present them with the idea that it could be wrong, then to outright say it is wrong.  The goal is to enable them to think for themselves, not to debate this or that belief.  Once they start thinking, they can easily figure those things out on their own.

When I first started doing research, I was still uncomfortable reading anything 'apostate', but still one of the stories that really stuck out to me was a guy that spoke of the "illusion being shattered", and that he started to doubt the "Jehovah's Witness fantasy".  Jws (myself included) generally never even consider the possibility that the whole thing's a sham.  It's just absolutely true and there's no alternative.  And if ever the idea pops into their heads they're trained to immediately disregard it, usually by thinking about all the fearful consequences of leaving.  

Jws are always in the role of 'teacher' in any conversation with a nonbeliever - it's completely one sided, they have 'true knowledge' and you don't, so they turn off their brains to anything you have to say.  So you have to bypass it somehow... talk about general critical thinking skills, and gradually move into religion.  Ask their criteria for determining if something is true or not.  If they're thinking critically, you can easily use this criteria to expose all jw beliefs, and if they're not thinking critically you can easily use their criteria to 'prove' things that obviously aren't true.  (or that are so unlikely as to be implausible)