[Source: Was NT developer - have code in NT 4.0...]

The big problem will almost always be some hardware dependency that breaks, almost always in I/O. I've seen video software used by TV producers that depended on an ISA (not EISA nor PCI, ISA) card to read NTSC input and impose text over it. And it broke as they were getting ready to add commentary to a live broadcast of a race (which I was driving in.)

The world is full of machine tools and metrology devices that are stuck on some ancient computer/software because they made a weird proprietary protocol over the top of a centronics connector, or some other "WHAT were they thinking??" construction...

All of these could be overcome with a new I/O device, and/or writing a device driver. So using say a raspberry PI that talks ethernet to your "monitor" PC is probably relatively change proof.

If there is any documentation, if anybody can find said docs, if there's budget for a new I/O card and the device driver to go with it. Often the parties who have those resources would rather sell you a new machine tool, metrology machine, or I suppose, nuclear reactor (:-)

Of course, certification is a big deal... A particular certification structure led to the 737 MAX tragedies. And since certifying authorities don't always have detailed tech knowledge of what things are, they have a hard time saying "no, you can't slide that by, you have to build and certify a new thing".