Eventual outcome of tidal acceleration and deceleration
So that's question 1: Is it really possible for tidal acceleration to
  throw a satellite into space before the planet is tidally locked, and
  if so, does either objects' size impact it, or just fluidity and
  relative periods?


During the locking process, the angular momentum of one is fed into the other until the periods match.  The final destination depends on the initial momentum of both objects and the moment of inertia.  As an example, if you make the moon less massive, or the earth more massive or with a faster spin, then the final configuration of the system would have a larger orbit.

You could certainly create a system where the final theoretical configuration has a distance to the satellite that is beyond the primary's Hill sphere.  Such a system would be expected to eventually separate.

Fluidity might change the rate at which the final destination is reached, but not its configuration.


  Will all non-retrogade tidally decelerating satellites eventually
  crash into their planet, or is it possible for the planet to catch up
  given the right starting conditions?


Each object is transferring the same amount of angular momentum.  But the response of each object depends (at least initially) on the relative magnitudes of their moments of inertia.  For a system where the satellite is (relatively) small, or where the difference in rotation rates is large, impact is inevitable.  The primary cannot speed up fast enough to keep up with the increasing speed of the descending partner.

But when the difference in periods is small, and the primary is small enough/far enough, then the objects would lock before impact.