Chad,
This seems like a rendering problem. I don’t think Skuid rerenders labels as fields change. Unless your field has a value when the form renders, you won’t see the label.
Take a look at this posting-> https://community.skuid.com/t/highlight-fields-that-are-required-and-empty
I run a snippet to rerender the form after the field that has a value changes to show the change in the field label.
Thanks,
Bill