For anyone that faces a similar issue. The fix was creating a setter and getter function in the parent class. For the child widgets, use the setter and getter functions in pre-construction. The secondary issue may have been an engine bug, a fix was checking if the widget existed, if not spawn it in and then use the setter and getter functions.
Essentially, the child blueprint was loading before the parent blueprint. I never figured out the root cause why the fixes would become undone, but thankfully that only affected the widget editor.