After the first few paragraphs, I was most eager to see how he managed to handle modern TLS on Win3.1. Last time I wrangled with vintage stuff near that timeframe, that was the toughest part.
Alas, he "cheated" for it with a proxy app. Can't say I blame him, since it's probably about as much work over again to get modern TLS 1.2 working on such an old Windows.
IMHO the fact that it's hard to get TLS 1.2 (or indeed any form of "pure" cryptography) working at all on an obscure platform says a lot about the state of commonly available crypto libraries --- as those who are against regulating it like to say, it's "just math"; and math that any computer should theoretically be able to do. OpenSSL is one of the more portable ones, yet I'm not sure how it would be able to handle the 64K segmented model. It would need at least 32KB (maximum TLS record size, multiplied by both directions) and a little bit more per TLS connection. That said, a 2048-bit RSA key is "only" 256 bytes, and ECDH ones are smaller, so I think a TLS 1.2 (or even 1.3) implementation on the platform is definitely in the area of "feasible, but not trivial". A lot of IoT stuff has similar constraints (minus the segmented addressing).
Alas, he "cheated" for it with a proxy app. Can't say I blame him, since it's probably about as much work over again to get modern TLS 1.2 working on such an old Windows.