That's a fair point. I just didn't think that there was that much "mission critical" legacy software developed specifically for the (not very stable) vanilla Windows 9X series. Most of the custom stuff I dealt with back in the day was running on NT, and later on 2000/e.t.c...
Well you have a fair point in that it shouldn't. But, i think you also know how things work in practice. Some things simply turn into dust until the day someone realizes it has actually become mission critical so that budgets can be found to do something about it.
There are quite some companies that never went the NT road, mostly for budget reasons and/or unfamiliarity with nt.
Also, on a broader note: I wasn't suggesting minesadorada try to run a newer Windows version on that laptop itself... but if the software he's using could run on a higher Windows version, why not just have a raffle or fundraiser or something at the golf society to raise money for a new laptop?
Yes sorry that is my bad. I actually wanted to respond on your initial statement: "I find it hard to believe that anyone is using Windows 9x anymore, for anything. What could the possible use case be?" but got mixed up with quoting.
As long as things are software only it should usually be fairly easy to port unless there is some real stupid things going on inside the code.