I'll take the current driver issues today over the driver issues of the past without a second thought. I still have a few pieces of equipment that run specifically off of MS-DOS and/or Windows 3.1 because people didn't bother writing drivers to exit protected mode for Windows 95 and so on. It was not uncommon back in those days for the equipment manufacturer to demand their specific computer setup including specific soundcard, video card, and so on for compatibility purposes, there was also some pretty pennies in the selling of those computers.
I'm going to take the opposing stance on this subject though, since I see it come up quite often. Some people will say the companies are lazy and such, there may be some truth to that, but in the end, you have changed, not the device and what it was designed to run on. Software is a very tricky thing, at the very best you can build a wrapper that basically tries to emulate the old environment, but the worst case is a complete redesign. From 13 years old to 23 years old I spent most of my time programming, especially in lower level languages, drivers were one of the things I touched a few times but eventually stayed away from due to their complexity and their pain in the arse debugging (without an ICE it's really tough). So, why rebuild the old project when you can start a new one, especially since you'll have to retest most every possible scenario to make sure a customer doesn't call up saying their app crashed halfway through that $50,000 print job and they demand satisfaction and blah blah blah.
To correlate this idea and place it in the signmaker's shoes: Say you sold a pair of magnetic signs for someone's truck, a few weeks/months/years later they went to put it on their fiberglass car and it didn't work, would you:
A. Redesign the laws of physics and change how magnets work
B. Refund the customer their money because you sold them magnets that didn't work on fiberglass
C. Tell them the magnets were designed for the truck, and that you would be more than happy to do vinyl for their car, but the magnets will not work on fiberglass and weren't intended to be used on fiberglass.