Hello everyone! I believe I had eventually figured out the problem.
So it seems when I declared my InputMappingContext as TSoftObjectPtr, this meant loading was deferred, and to properly load the Object into memory I needed to call MyObject->LoadSynchronous(); for things to work properly.
Additionally it’s been a few days since I posted this and determined the solution, but I also believe that separately I also had an issue where LoadSynchronously wouldn’t work in the Constructor; because it loads before the Editor context or something? I don’t quite recall the exact explanation. But anyways, the LoadSynchronous() call also needed to be in BeginPlay for the Object to be properly loaded into memory.
Alternatively to avoid this hassle, I could use just a regular pointer for InputMappingContext which when assigned in the Editor would also work perfectly fine. As there is no likelyhood of a “Dependency Chain” from what I gather TSoftObjectPtr didn’t provide any benefit for this situation.