As it happens, without wishing to tempt fate, I've not had any problems with Windows Updates recently. Since I've got my new laptop and desktop PCs, I hardly notice them.
With regards phone updates, I can only relate to Android, and we usually get a security update every month (or perhaps two), and a major OS updated once yearly. The security updates are not usually a problem, and take about 20 minutes all in all (including download time), but the annual OS revisions usually break something that worked perfectly well before. As Android isn't quite the 'walled garden' Apple is, Google tend to make changes that mess up existing apps, which then take time to catch up. It's not always an issue, but they've messed up the music apps and playlists over the last two upgrades, and they are still not really working as they should. Since the latest upgrade there is now a delay with music apps updating with anything that is added to the SD card. I would actually quite like to switch back to an iPhone but the thought of of having to replace all of my current apps is a bit of a nightmare. Ten years ago I would have relished the prospect of a new toy, but these days I can't be arsed.