I can contribute answers to some of those questions from my tests with the team at the event. I just can't try it again now.
The service was listed as running after the failure occurs. Stopping and Starting the service cleared it up as you would expect.
With the Classmate change:
- The first (team) Classmate exhibited the problem during build season, but for other reasons we restored it from scratch and reinstalled the Updates. After the Restore, I had them uninstall the Cypress software, then install DSUpdate1.0, followed by DSUpdate1.1
- The 2nd Classmate was from Spare Parts and as a week 1 regional it got updated when we came in on the first morning.
While I did look at the PSoC version number, I cannot confirm that because I don't have a firm memory of it. I can only remember that I was happy with it at the time.
The Classmates were generally booted without the IO board connected.
The IO board was plugged in afterwards.