Assuming the KVM switch, and related infrastructure, are well-secured, I don't see how Windows 3.1 vulnerabilities would matter.
(Not sure if the job requires feeding floppies and/or CD's into the machine, which AFAIK isn't something solved by any off-the-shelf KVM switch.)
>SIEMENS Sibas 32, 6FH6035-1A + 4x 6FH 9543-3BY60 + 6FH 9533-3BY60 + 6FH 9550-3AY60 + 3x 6FH9485-3A + 6FH9484-3A + 6FH9498-3A + 6FH9481-3B Antriebssteuergerät
7500 EUR, 28 kg (found after a quick search).
This is my point, actually.
You wouldn't be directly connecting the PC to the Internet. You'd connect the PC to the KVM switch's PS/2 and VGA connectors. The KVM switch present the corresponding virtual desktop to an appropriate user over the Internet using RDP or similar.
Again, I'm not sure such a product currently exists, but I assume it is, given the needs of data-center admins.
The salespeople probably make jokes about high-speed computers.
I have actually used "Windows 3.11 for Workgroups" with some coaxial-cable Ethernet NE2000 cards, but I do not remember what network protocols were used.
With all earlier MS-DOS or Windows versions third party networking solutions had to be used.
Periodically someone somewhere would plug both ends of an ethernet cable into the wall sockets, causing a broadcast storm and every PC in the building would freeze - Not even the mouse pointer would move.
*Update:* Yes, looks like it uses the networking stuff provides by MS-DOS.
MS-DOS has NETSTART.BAT and PROTOCOL.INI that initializes TCP/IP with IP address and subnet mask.
When you look how a passenger information system in the trains boots up you can see how it shows BIOS information (floppy drive connected, serial and parallel port available, no harddisks) then it boots MS-DOS, initializes a XMS RAM disk, initializes parallel port, loads Crystal ENDS2ISA ethernet drivers, microsoft DOS TCP/IP protocol driver, and TCP/P MEMM driver, and calls NETBIND.COM.
https://en.wikipedia.org/wiki/Novell
Oddly enough my MS-DOS machine while in grad school was networked via a product made by Apple that allowed it to connect to a Mac network. My only use was accessing the department laser printer, but that was huge.
I guess with some luck you can work on these hardware drivers for Windows 3.11 at home without any access to the network or train. What you need are specifications and maybe some part of the system, maybe there is some simulation software for the internal system of the trains.
I mean the alternative is that you have to work in the train.
*Update:* Since the SIBAS 32 system is just a box someone can sent home to you, you can probably connect a computer with Windows 3.11 to it, and run some simulations on the SIBAS system.
No it doesn't. You can run your exploit code and then crash the program, same as exploiting any other program. Or you can add some minimal code on the end of your exploit payload to exit cleanly. If you really wanted to gold-plate it by having it resume the program where it had been then yes, you'd need to figure out some details, but that's not normal or necessary - classical "smash the stack" style exploiters rarely tried to unsmash the stack afterwards, they'd execute their payload and then exit or crash.