Your argument is similar to the “what use is half a wing (or any eye)?” question.
The answer is, “more use than no wing (or eye) at all.”
Any proto-wing or eye may not be a “small, useless appendage,” but something that enables the proto-bird to escape from a predator better than one without.
And no, half a wing doesn’t mean a full one only on one side, but a partial development in a symmetrical fashion, which is much more logical and likely.
Anything* is possible, but the question is whether it is probable. Absent a change in the environment, there is no reason to speculate that flying squirrels will evolve into bat-like creatures. Certainly not in the time frame mentioned, and especially given that there are 50 or more species of flying squirrels that have been around for millions of years and none of them has started to look like a bat.
As **Blake **said, we know next to nothing about bat evolution, so we don’t have a good model of going from non-bat to bat.
So, given that this is GQ, if we want to speculate about what is possible, then pretty much any post anyone makes could be called pertinent to the question asked. I think we are better served, in this forum, to concentrate on what we know and leave baseless speculation to other forums.
*anything that doesn’t violate the laws of physics.