Reminds me of people who know little of the field of computing and the efforts involved and think that solutions spring out of just saying "it's easy, why don't you do it?!".
No, it's not.
Rewriting the software is probably not much of a problem but the paperwork around it is.
Or - you can use the existing Win3.11 systems, which are apparently still working just fine, and just update and test a single application.
I can lend you my Petzold, if you like.
A system that old that has been working for as long will surely have so many quirks, exceptions, bugs and workarounds deeply engrained in its users' processes. A naive port and rewrite will probably need many man-months of lost productivity spent recreating all the quirks of the original piece of software, resulting in an even less maintainable second iteration.
I’ve done some wild shit in my day. Gotta think outside the box and go to first principles. If it looks like a duck, quacks like a duck and walks like a duck it’s a duck. You can replace things pretty easily when you identify the perimeter of a piece of software.
These days we have pretty powerful decompilers too. I’d posit I could replace this tech for the same cost of one year of whoever they are hiring for this to perpetuate the antiquated crap.
"Oh yes, we missed that one output that only happens under these specific conditions and now the train crashed – oops!"
“Hey, our software works and is certified but it’s ancient and no one knows how to maintain it. If was written 30 years ago on a version of windows that doesn’t even support the internet. We need to upgrade and recertify”. This is an easy argument.
I assume in the newer trains they already recreated new systems. For the old trains it's just not worth it to modernize, as it's incompatible with the newer trains and thrown away eventually.
And who knows, maybe they gave it a try in the past, and it did not work out.
What you wrote reminds me a bit of a friend who asked me 15 years ago when he installed Java: "Who uses Java anyway?". You just have to change your perspective from an end-user. Same for Windows 3.11.