I actually believe that I found the answer to my problem.
I found that the issue I was that I was creating a DataAsset (Using Content Browser → Miscellaneous → DataAsset) and having that asset be a child of my C++ UDataAsset class.
The fix for me was instead of creating a DataAsset to inherit from my C++ class, I instead created a normal Blueprint to inherit form that C++ class.
I’m not sure exactly what is going on under the hood that is causing the difference here (If I’m being honest I didn’t really look into why this was the solution)