The cylinder is not cutting the family solid, so it cuts the host element in the project (this may not be what you want, but it cannot be avoided!)
the rectangular void is not cutting the family void, so it cuts the host
Tick both boxes – only the rectangular void cuts the host (as it is not cutting the family solid)
The cylinder now cuts the family solid but not the host (and is no longer visibly ghosted)
Conclusion
If the void cuts a solid in the family, it cannot cut an element in the project using the ‘Cuts with Void When loaded’ family property
If the void cuts a solid in the family,the new (in v2021) ‘Cut Geometry’ property has the potential to work in a project
If the void does not cut a solid in the family, it can cut an element in the project using the ‘Cuts with Void When loaded’ family property – but only when you use the ‘Cut’ command in the project
If the void does not cut a solid in the family,the new (in v2021) ‘Cut Geometry’ property has…