Back then you had to be super careful about creating a strong product that wouldn't require too many updates. Now you have CI churning out multiple new versions a day, but one could argue we've got lazy about quality & documentation. And for the power user it was good to have complete control over whether you installed an update (and equally bad for the company because it was hard to know who had what version).
These days you have to look for release notes, newsgroups, Slack channels, Discord channels, tweets, FAQs, KBs, and so on to make sure you know what's going on. Gets a bit tiring. As a web developer I of course love the fact that I always know what version of the software my users are on, modulo browser differences.
Not arguing for a return to the past, not at all. I'm just saying that after 30+ years as a developer I don't feel that we've served customers any better in 2020 than in 1985.