Yep. It became a real shit storm when they changed the driver system somewhere around Vista/7 and people found they could no longer use their old(-ish) printer with their new computer. Then again, that same backwards compatibility has been a major contributor to all the security issues over the years.
The difference is that the browser is now the center of computing for most people; things are thrown away quickly if they're not actively updated and 20 year old web pages render (mostly) just fine. Compatibility for an OS isn't needed near as much for most people most of the time only need an OS to launch a web browser. Hence Chrome OS.
There's a reason Windows XP has stuck around for so long... most people don't need anything beyond XP. Sure they need security updates and new drivers, but these things are in the background. XP had, essentially, everything anybody will need for the next 50 years.