Computer software is mostly designed and written by young technophiles, fond of new and clever things. It is largely used by old non-technophiles of conservative tastes, people who would rather not have to learn a new interface and a new way of doing things every year, not even every decade.
That suggests the need for a middleman, a firm standing between software producers and users, providing the service of making life easier for the latter. Part would be pointing them at software that still works the way they are used to, part showing them how to configure the new version of a program to make it as much as possible like the old. Part would be telling them how to get at files written under software that no longer runs on their current hardware and operating system.
I have come across a couple of solutions to that last problem but know of no way short of an extensive google search to find more. WriteNow is an elegantly written word processor not available for decades — but OpenOffice can read WriteNow documents. MacDraw was long ago consigned by Apple to the trash heap of history, but EasyDraw, not the current version but one of the older versions still supported, can open documents created with MacDraw. There are doubtless many similar cases. If all else fails, the user who insists on sticking with his long obsolete software, perhaps a favorite game, could be given detailed instructions on how to emulate an old machine on a new one, along with any necessary software to do it. Running a program in emulation is considerably slower than running it natively — but current computers are a great deal faster than the machines the old programs were written to run on.
It looks like a market niche so far unfilled.