Point is, its now unsupported, so its good as broken... In fact, if you need win 95 to run it, its been broken for a long time now. The longer you delay that upgrade, the harder it becomes.
The point is you have equipment that is worth millions of dollars and even more in downtime that is reliant on half baked software made by the OEM to only work on there equipment and will only run on say 95.
Its not a mater of won't upgrade, its can't upgrade. Had this not so long ago, one farsical example up until a couple of years ago still required DOS. Hell being able to use XP on these things would be a god send.
Apart from when I actually worked in IT. At no point did they have any control over the computer hardware attached to any equipment that i have used.
Basically the case in the industry I'm using as an example. The problem we have today is a lot of the IT people these days are more of a ghost stuff and reload packages type people. A lot of the ground level diagnostic software is usually dealt with by one of the ground level end users who has the "nerd" skills to try and sort it.