The thing is that date setting is the only thing that keeps JWs motivated. I was just a young kid during the 75 debacle but I do remember the energy and excitment thinking that the great trib was going to start any day now (fear too, but that's another story). I also remember the argument about how Adam was created 6000 before 1975 but we didn't know when Eve was created or when they officially sinned. To me, the generation teaching was the primary argument that I (stupidly) believed meant that the world was ending soon. It fit together so nicely.
I recall giving a PT about the last days (early 90s) and even using the argument that we were almost at the 80 year anniversary of 1914 and that generation didn't have many left.
The change in 95 took the wind out of 1) the sails of folks that stuck around after 75 (like my parents that were in their 20s at the time) and 2) the born-ins like me who suddenly realized that we had better plan on getting a real career, get married, have kids and try to live a normal life because there was no longer a end date in sight.
The effects of having no date took a while to manifest but compare the "zeal" of your average JW 20 years ago to the average JW now. There is no comparison! It's obvious to me that leadership needs to fire up the members in some way. The best way to do that is to set a date. While I'm not sure they'll make the same mistake they made before, but I would be willing to put some money on it. After 15 years of dwindling committment levels in first world countries (where the donations come from), I firmly believe the WT leadership is aware of the problem. The berating talks, guilt inducing WT studies, pressure from the CO & DOs, placement of MTS grads, none have really worked.
Sure, they've had growth but its not translated into enough cash to keep the status quo. So, they've cut expenses to the bone (with more cuts on the way I would imagine). They have to figure out a way to motivate the average JW in the developed world to give more. In my opinion, there are 2 ways they can go:
1 - Mainstream - drop shunning, make blood conscious matter, focus less on field service and more on community projects (sort of like the LDS), turn Bethel into the JW version of BYU, push getting a good education instead of vilifying college, etc. Still keep the whole end time thing like others have but make it much more nonspecific, keep the no trinity, no hell, maybe no holidays. Institute tithing at some point so they can reasonably budget and make a go of it. Sure, you'd lose some members but I would bet you'd keep more born-ins who view JWism as just another religion. You would likely increase cash flow.
2 - Set an end date at 2034 and attempt to repeat the amount of growth they got in the 20 years prior to 1975. Sure, 2035 will roll around and the world will still be kicking along and there will be fall out from another false prophesy but if you could increase the numbers from 7 million to 14 million, who cares if you lose even 25%. It's not like they haven't done this before.
If they keep going the way they do, I see a slow death by a thousand cuts. #1 would make the most sense from a business prospective but I don't see them resisting #2. Time will tell.