I think the old days (1980s etc) it worked because PCB CAD was moving people from drafting film + tape to CAD, and same for circuit drawing. So there was
mass adoption and a lot of $$$ was being made, even at $500 per user.
After everybody had moved, say c. 1995, the money stream dried out and companies had to find other ways to make money. So we got a load of crappy buggy updates, each one fixing 10 bugs and introducing 11 new bugs.
Altium's replacement for Protel does way more but they are trying to get 20k from you (last time they phoned me, maybe 10 years ago) whereas Protel 2.8 was about 1.5k. The guy came down to under 10k during the phone call but I still didn't go for it

The business will stabilise at some much lower level than the good old days and at very high price points, and cheap software will dominate the lower end.
Back to Windows, all the time we hear the corporate BS about "security" (when actually most attack vectors are via the browser or email client route, not via somebody hacking your PC from outside and doing super clever tricks to penetrate NAT) most people will just keep upgrading.
I will try out 99SE shortly

Thanks massively for the tip about avoiding the stupid crazy client-server model!