Well, as long as noone conclusively wins outright, we will have a standoff that will leave Miners on Legacy Chain very much obliged to slowly move towards UASF chain with the growing risk of reorg.
Doubtful. I would expect that the legacy chain will leave the UASF chain in the dust, with no hope of ever coming close to such reorg. Even if it did, however, there are trivial means to ensure such a reorg does not occur (e.g., invalidateblock).
I am not so sure. UASF only needs 51% minus the share of the biggest pool. If this pool is as big as it is said, then they need very little for all the other miners to have a clear incentive to move and not run the risk of being moved on.
I hope it fails, because of how it was handled. But I do not think it is farfetched.