I don't understand the snark. This seems to be an installation that hasn't changed in a while. And very likely is not connected to the internet. As long as it works for the operator, there is no need to change the OS, especially if that also means writing the bespoke software from scratch as in this case.

I'd be mostly worried that some part of the hardware resigns as it may be difficult to find a replacement or spare parts.

EDIT: The machine is here (German tv report), and the owner is indeed mostly worried about the hardware as everything has been running smoothly: https://www1.wdr.de/wirtschaft/landwirtschaft/-windows95-due...