E-mail on older systems
Lately, I've been trying to get my AOL e-mail working again on my older machines. After much searching, I found an application called stunnel, which is basically a local e-mail proxy server that allows you to connect to SSL-based IMAP or POP3 e-mail providers using a non-SSL-aware client.
The main website for it is here: https://stunnel.org/
Unfortunately, it seems they've discontinued win32 binaries, opting for 64-bit only. However, there is a user-provided binary for 32-bit Windows which can be found here: https://github.com/josealf/stunnel-win32
And here's a screenshot of Netscape 4.79's e-mail client, working again for the first time since AOL discontinued basic IMAP support a few years ago:
Edit: Upon reading further, this is not just for e-mail - it works for many protocols, which means it should be possible to use it for WinWorld's r-type IRC. I'll update this again after some more experiments.