I should clarify something–my experience was that the problem could be replicated with Ableton Live as long as I was sending automation that had one breakpoint per MIDI CC value. 

In other words,  "straight line" automation (a line with one breakpoint at each end) did not recreate the problem because, as  MIDI monitor reveals, this particular automation did not send the full range of MIDI values. It thins it out and sends every third or fourth value. 

For this test, I recorded the automation from my expression pedal (A Dunlop Volume X being converted to MIDI with a Decibel Eleven Switch DR.) I wanted to see if the pedal's output looked particularly weird, or was sending any other messages I didn't know about. It also allowed me to test at different tempos to figure out how fast is too fast.

I would be happy to send you a Live set with the automation I'm speaking of. It would be interesting if you see the same results since you'd be sending the exact data generated by my pedal.

Otherwise, I will post more detailed results, and results of other controllers that can recreate the problem when I have a little more time.