> as though subscription software is something which has been sneaked in on us
Oh but it has (IMO).
> users today expect things like instant updates [...] constant bug fixes and patches
Nah, this is in reverse. With boxed software, the developer had to deliver an essentially bug-free product. Now, with easy updates technically possible, the developers have gone complacent, and deliver shit. That is why users expect bugfixes instantly. (And any enlightened user abhors unrequested features, as there are no features without regressions, and who wants regressions in any serious application?) The only tolerable online updates are security fixes.
> sync across devices, collaboration
This is a valid expectation, but its execution has been a train-wreck. Research, design and implementation should start with end-to-end encryption; the network architecture should be peer-to-peer (mesh, not centralized). What do we get instead? More centralization of control than ever, and less privacy and ownership than ever.
Generally that's not how I remember it - third party software on the Mac at least got some kind of a beach-head because Windows software was full of bugs, crashes, corrupted files, drivers that never worked, and patch CDs mailed to enterprise customers like they were firmware apologies. Own your own software, taken to its logical endpoint, was a shareware nightmare.