Hi,
I did more digging and figured out the actual cause:
ControlsBinding depends on KeyBindDynamic…
…and KeyBindDynamic depends on ControlsBinding…
This is why ControlsBinding was getting batched together in the fashion I described in my original post. I was double clicking on the ControlsBinding blueprint to load it, and it would load all its dependencies dependencies…which turns out would cause it to load itself when it loaded KeyBindDynamic.
This leads to the failure conditions described above.
This bug can be closed. It would be super awesome to have a circular dependency warning if possible. It would’ve saved me a ton of time.