I have some familiarity with hippie/liberal west coast JWs as well as fundie/conservative red state JWs. This may seem counterintuitive, but it can be quite difficult to help the liberals see the light about the organization.
Liberal JWs can rationalize the craziness among the right-wingers by saying "they just aren't doing 'The Truth' correctly." In other words, a JW raised in a liberal congregation thinks that the JW org is like liberal, reasonable, etc.--and the fundie/judgmental/hypocritical stuff is an anomaly. Of course, those of us who have been around the block know that this is not the case.
On the other hand, those of us who grew up in hyper-conservative areas/congregations often have years of bad experiences that eventually lead to an awakening.
And often it takes a bad experience to awaken a JW to the cold hard facts about this religion. It is very rare for a JW to be in a reasonable congregation, have good friends in the congregation, and have a peaceful JW family life...and all of a sudden decide to question his/her beliefs. Rather, most JWs don't start questioning their beliefs until something happens to THEM--for example, if THEY are the victim of an elder's vendetta, or if THEY have a family member or close friend DF'd. And this sort of thing is more likely to happen in fundie/conservative congregations.