Compatibility of software installer

Hi,

I need some information related to the compatibility of a software application being developed in my organization 

Requirement : To test an installer for a .net application if it installs that service properly on mentioned OS :

- Window  10 Pro
- Window  10 Enterprise
- Windows Server 2012 R2 Foundation

- Windows Server 2012 R2 Essentials
- Windows Server 2012 R2 Standard
- Windows Server 2012 R2 Datacenter

- Windows Server 2016 Essentials
- Windows Server 2016 Standard
- Windows Server 2016 Datacenter

- Windows Server 2019 Essentials
- Windows Server 2019 Standard
- Windows Server 2019 Datacenter

Questions

1) Do I have to test my installer on all of the above OS or I can safely assume if it's being installed properly on Windows Server 2016 essentials, it must be compatible with datacenter and standard versions of the respective windows server

2) What would be the best approach to install different OS in less time on any VM and what additional things I shall take care of to ensure that installer works fine w.r.t. first time install, repair and then uninstall the program