Hi Bill -
It took me quite a while to piece together what you are trying to do but I think I’m understanding your intent. From that understanding, I believe I have figured out what your issue is and it has nothing to do with Grids, Collapsible Wrappers, etc.
Unfortunately, you have stumbled upon a Skuid bug that appears to be specific to Button Sets.
I have posted the issue at ““Remove All rows in Model” action breaks conditional rendering on Button Set Buttons” with an isolated repro.
If my understanding of what you are trying to do is accurate and based on my findings with the bug, I believe the only workaround for you (until Skuid releases a fix) is to use a Page Title Component instead of a Button Set.
As you’ll see with the isolated repro, boiling down complex use cases to simplified versions using standard objects makes identifying the root cause much simpler 
