Can't update project to UE5

But you are not copying the content directory via Windows but using the Unreal Editor with the “migrate” function? In the editor you also have the “Validate …” and the “Update Redirector …” functions when you right-click on a directory.

Otherwise I would try a new C++ project and start the editor via Visual Studio. In the event of a crash, VS will then show the point in the code that caused the crash and you can then search for solutions.

Perhaps also take an intermediate step with UE5.0.