Fortunately I’m not competing with windows :). But real talk, I only have 40 hours a week and I put a lot of energy into providing my users features they ask for. In return, I ask of them to make it easy for me to continue to do that.
If you look at any company’s internal tooling, this is universally well understood. Migrations and upgrades are a pain in the ass in the short term but a net positive in the long term. I don’t want to break their systems, but software evolves over time and if you expect something that worked once to always work, that’s not realistic expectations for any software I’ve ever been a part of.
I would argue the notion of "it stops working" is something acutely unique to computer software (and hardware to a significantly lesser degree).
Think about it: A computer is a tool, but most tools never "stop working" per se. That screwdriver? It used to work when it was first invented and it will still work a thousand years from now. That car? Keep it maintained and it will take you places for at least the better part of a century. That boat? We can keep boats floating forever.
Computers are one of the few, if not only, piece of tool that demands it be replaced every few years, and it probably hasn't even broken down yet which would merit a replacement.
> That screwdriver? It used to work when it was first invented and it will still work a thousand years from now.
Maybe it did not and will not -- old screwdriver is probably flat blade, now people use Philips or Pozidriv screws and in some time most will be Torx.
> That car? Keep it maintained and it will take you places for at least the better part of a century. That boat? We can keep boats floating forever.
The same: the fuel and oil is changing (maybe you will not even be able to source gasoline in 2050 if everyone migrated to electric vehicles), and specific spare parts are no longer manufactured.
I guess with large old boats also come expensive support contract - similar to paying someone for a super-long-term individual software support.
> Computers are one of the few, if not only, piece of tool that demands it be replaced every few years, and it probably hasn't even broken down yet which would merit a replacement.
Computers are also relatively new and quickly advancing in features, while the other examples you have mentioned were mostly "stable" for 100 years.
If you look at any company’s internal tooling, this is universally well understood. Migrations and upgrades are a pain in the ass in the short term but a net positive in the long term. I don’t want to break their systems, but software evolves over time and if you expect something that worked once to always work, that’s not realistic expectations for any software I’ve ever been a part of.