IMO we could learn something from the Commodore 8bit market. Most users accepted the platform as a retro hobby 15+ years ago. Many Amiga users (and companies) still expect the Amiga to take over the world, which is far too unrealistic of a goal.
Surely nobody left is that naive?
For instance, Hyperion market OS4.x with the "Remember when computing was fun?" line. That doesn't tend to suggest they feel it's going to be a workplace contender to me.
Speaking of 8-bit, did any of you guys ever check out the BMOW (big mess of wires) project?