Widget_GameHUD contains Widget_Abilities_Box (second custom widget) which is made of an horizontal box with 6 Widget_Ability_Box (another custom widget)
Could you use the reference viewer to check for circular dependencies? If you find any could you try and break these for testing purposes and let me know if the issue still occurs when there are now circular dependencies?
In our case we had issues with deprecation. We had a parent class for the widgets (c++) that were deprecated. Widgets kept displaying correctly. After making changes to the widget containing the widgets with deprecated parent, they simply were gone after editor restart.
The editor was throwing deprecation warnings for another widget after the change, but not for these. Changing the parent of the affected widgets to UserWidget resolved the issue.