Stand alone executable are very easy to support for ~20 years on the windows platform. It's only dos games that need to be packaged in VMs for modern platforms.

Stand alone executable are very easy to support for ~20 years on the windows platform. It's only dos games that need to be packaged in VMs for modern platforms. Support only becomes a problem when there's invasive drm tied to a specific os or hardware platform or required online services that require ongoing maintenance.