Well, I wanted to get enlightened about especially this conflicting facts:
running on a Linux or OSX machine
vs.
There is nothing (…) that requires me to have any other system, not even the TLS issue
They are two solutions. Jubadub is talking about using Cameron Kaisers
Crypto Ancienne library with it's built in HTTPS to HTTP proxy application
carl on MachTen on Mac OS 9.2.2 instead of running it on a separate Linux or Unix machine. I'm talking about STunnel for "bridging" TLS/SSL mail servers to email clients with no TLS/SSL support (like anything other than the Classilla email client on Mac OS 9). I have never tried to build STunnel on MachTen, so I don't know if it will run in that environment.
So not conflicting, but two separate things