Earlier quoted context omitted.
> The oldest OS that qualifies for interacting with these systems seems to be Windows 3.11, so it seems knowledge of such a system would be part of the requirements of a field engineer Working with it, yes. Developing for it? Completely different game, as you'll have almost zero chance to use anything modern, and that includes the tooling.
People are building Amiga applications as well as games and scene demos for much older 8-bit home computers with modern development tools. Even if Windows 3.1 doesn't quite have the same enthusiast following I would expect that it's possible with a bit of reverse engineering and tinkering (especially since Win3.1 is still quite small and simple). TL;DR: I wouldn't be surprised if it's harder to support Win8 today tha…
Yeah but these things are built from scratch. Your average ages-old Borland or whatever suite with its build script? That's a lot of work to integrate with a modern IDE, and honestly I wouldn't risk it in that space either due to the potential for things to go horribly sideways. So you need at least the OS and build tooling combination that was used for the last certified build, and if certification requirements are really strict you can't do that in a VM but have to develop on age-appropriate hardware as well.