Well - for those who might find themselves reading this post (unlikely), I believe I found the issue with the "hanging". Interestingly, it seemed to only happen on the far outer parts of the Contour shuttle - the Shuttle In Left 7 and Shuttle In Right 7. It didn't seem to matter what I put in those positions - they freaked out CbB. I could even put a known working command at 1 pres every 2 seconds and it just did this weird on-screen hang. The display didn't update, yet the time was actually moving. When released, the time was in the place it would have been if you had seen it moving all along, but you never actually saw the motion - just the end destination.
In the Contour Shuttle dialog, there is a setting under options to "disable speed control". The definition of this in the documentation and forums indicates that it disables different speeds from happening, but I don't know really what that means. Maybe for certain kinds of assignments.
Anyway - if I assign the "Shuttle In Left 1" to 1 time per second up to "Shuttle In Left 7" at 60 times per second with the "disable speed control" checked, it works just as you would expect by the keys assigned to each thing. In other words, as I move the outer ring further to the left or right from center, the speed of transports FF or RW increases - and it does not hang up at the fastest speeds.
So - problem solved. And now documented for all to Google.