I would more characterize it as failures in their mobile space. Microsoft has rebooted it's mobile product line a bunch of times. But, as noted, my Lumia Icon was a Windows Phone 8.x device, and it runs yesterday's release of Windows 10 Mobile. A pretty large number of 8.x devices are capable of 10.
The manual intervention to upgrade to 10 is because, as noted, the big change is that Windows 10 Mobile upgrades are handled by Microsoft, so the update servers had to be changed. Prior versions to 10 had the same carrier-based update issues Android had.
I'd argue that change alone points to the fact that Microsoft is getting better at long term support, not worse.
The manual intervention to upgrade to 10 is because, as noted, the big change is that Windows 10 Mobile upgrades are handled by Microsoft, so the update servers had to be changed. Prior versions to 10 had the same carrier-based update issues Android had.
I'd argue that change alone points to the fact that Microsoft is getting better at long term support, not worse.