I'm not an expert in particular game launching problems that there might be - although I know that Windows 10 itself has many with state of the art games.

But for the actually problem status, perhaps for others to give you a better idea, could you verify these:

- initially, you say that upgrading VMware started the problems

- however, in the above you say that VM-computer upgrade started the problems. Can you verify which is it?

- are you really using Player or Workstation Pro? Pro gives you easy upgrade choices ... not sure why you would need to upgrade the VM-computer itself, you can run lower VM-computer versions with newer Player/Pro version in a rather flexible manner (if you don't need some of the new features).

- has your Windows 10 had a Feature Upgrade associated with the problem timing? This is well possible to cause problems, even security updates could do that. So, with your current Windows 10, does it work, in some case (not sure what case that might be, check the questions above)?

Anyway, I think any of these 3 matters (Win 10, software upgrade, VM computer upgrade) can cause a certain problem, but it would be good to limit the possibilities. In games, you probably use 3D acceleration in the VM and thus the problem may be because of combined problems (like new VM software version trying to access new Host graphics driver versions ... or something).