Like all authoritarian regimes, the WT is reactionary, not strategic in the long term sense of the word. At present, they have no reason to "dump" 1914, so they will not, however...
The recent rebranding efforts are a sign that they are captiulating to social evolutionary pressures. The dates and esoteric nonsense that used to be the mainstay, are no longer stressed, since most of these can be very easily demonstrated to be untenable. That was much harder to do pre-internet, so there was no reason to move away from that particular "product". It was what made the WT different, and they reached a niche market that way. They have decided to move away from most of the old pseudo logical approach in recent years, not exactly as a deliberate effort, but rather a reactionary one as their own need for survival dictates. They never would have bothered with jw.org if they did finally see that their very existence was threatened without a, (seemingly), meaningful web presence, with all of the outward sparkle that goes with it.
Just as with implementing jw.org, they will not bother to remove 1914, until stressing that date becomes so untenable as to require it for their survival. What jw.org will do for WT is buy it time to complete the rebranding process, and, (hopefully from their perspective), use that rebranding to complete the process of eliminating the esoteric bent of the WT altogether. If they are "successful", they will create an organization that is focused on their particular alternative lifestyle, and nothing more. But again, this is not really a focused deliberate effort, so they will stick to 1914, and some other key esoteric teachings, until at which point it becomes more painful to keep them. They would rather do nothing, if they could.
I do not believe the WT will survive that transition ultimately, at least not in any recognizable form.
d4g