Ah, the good old days. I ran a BBS in Sweden with ProBoard. Anyone else used that for BBS'es here?
My OS of choice was OS/2 Warp. It could handle a full-time, two-node BBS and still allow me to do other tasks without skipping a beat -- all on a 486 with 8 MB of RAM!
I also remember being rather envious of how cool Renegade, WWIV and company looked. Not to mention the more exotic software powering the, er, rather more questionable boards: software with ominous names like ViSiON-X or Oblivion/2... But after trying them all, I eventually switched from TriBBS to PCBoard.
It was the right choice: I loved the flexibility of PCBoard's scripting language and C SDK. Adding functionality to my BBS is what prompted me to pony up for Borland's Turbo C++ and get serious about programming.