Hello
Thank you for posting in Microsoft Community forum.
For your first scenario, where you have two virtual servers on the same physical server with 20 simultaneously connected computers and 60 different users (not simultaneously), you would need a Windows Server 2019 Standard license. This is because the Standard edition allows for two Operating System Environments (OSEs) or Hyper-V containers.
As for the Client Access Licenses (CALs), since you have 60 different users, you would need 60 User CALs. This is because a User CAL allows a user to access the server from multiple devices.
For your second scenario, the Windows Server Essentials edition is designed for small businesses and supports up to 25 users. However, it’s important to note that you cannot have more than one Windows Server Essentials License on the same physical server. Therefore, if you need to support more than 25 users or require more than one virtual machine, you would need to choose the Windows Server Standard License.
Best Regards,
Wesley Li