Of course, lifetime upgrades of licensed software didn't really either. They didn't go away immediately with a canceled service, but in most cases they still end up breaking with OS upgrades, new devices, etc.
The difference being, upgrading the OS was your decision. You still had a license for something that worked on a dated version of the OS, if you so chose.
Kinda sorta. Security patches. There's other software you want to upgrade that's only supported on newer OSs. Your hardware breaks and the replacement hardware needs a newer OS.
Yes, it's possible (and organizations with specialized needs do) keep running 15 year old software and hardware without changing anything. But, for ordinary people, that app you bought is going to break at some point in the absence of updates. Of course, it's a bigger problem with SaaS and you have less control over it but licensed software is not immune.
"we initially made a higher priced plan to get more from our customers for the same, since we'd have supported all our customers anyway since broken or dated software would have put us out of business. But now that we're commercially stable, it's time to moralize about how unfair a burden our voluntarily offerings on the market are to ourselves!"