My cynical strategy: Let the deluded old men keep changing their ideas. Let them make these pivotal doctrinal changes (eg. the generation) frequently. Let them come out with articles that try to support the weakest links (eg. 607) and monitor the net for feedback and counter arguments. As the jw userbase grows disaffected, a faction within the hierarchy of the Org can prepare for a "Reformed Jehovah's Witnesses" non profit to be setup and in waiting, ready to quickly come into being.
When most of the current 70,80,90 yr old JWs are dead and gone, and they've hopefully gotten something from their wills, then the faction that will represent the new reformed non profit can begin to make use of a new feature of the WT. Not the current "questions from readers" farce but a more harder hitting section that serves as a discussion on alternative views. The faction can use this section in a series of magazines to instigate debate, bring in fresh ideas, and tap into the actual opinions and beliefs of the rank and file...the ones that actually care about it. The more nonsensical teachings from the current JWs can serve as a pretext for needing to split.
If there's momentum, they actually make the split. They'll lose alot of followers but they're going to shrink anyways. See how many followers go to this reformed movement. If it makes sense, the old WT can just dissolve, seeing the error of its ways, and gift all its assets to the reformed movement, that can choose to liquidate or make mass changes as it sees fit.