It's just sad to be required to run Windows 3.1 in 2012.
My friend sent me a video today of some guys hacking on Mac OS 9 at a hackathon he went to and it just felt odd to even look at it. It's been a solid decade since I've seen OS 9 alive and breathing, it feels like a friend who died long ago or something. And as far as Windows goes I don't think I ever saw anything before '98.
It's a peculiar feeling.
Another person I help is in the newspaper business and does his layout with PageMaker on OS9, Iv'e been trying to get him over to InDesign but Adobe left behind a lot of the keyboard shortcuts he relies upon and its been a unsuccessful venture so far... As each year goes by its getting harder to find compatible hardware and currently the internet needs to be done on OSX... Would do it in classic mode on OSX but some of Adobe's rendering routines don't particularly like OS9. Talking with him about it many other papers still use OS9, mainly because like the OP said - "it just works" and I can understand their dilemma, when we have tried transitioning things, stuff doesn't "just work" anymore.
I have a Blackberry from about 7 years ago that won't even connect to my computer, but it's reliable. The battery lasts me 2 or 3 days, the software is perfectly stable and responsive, and I'm just used to it. I imagine the software it runs is insanely old and out of date, but I have no desire to replace it. It just works. So I understand the sentiment. Although as a developer I try to keep pretty up to date on my computer :P
The surface mount pick and place machine runs dos 6.x and win for workgroups 3.1x
God only knows what the oven runs.
It is weird, but then again it all works.
At least for him, 640K turned out to be enough :)