[lugged]

Which distro?

You might want to look into something less unstable.

I've had arch running unattended upgrades in a Cron for years.

Worst case I have to find my USB stick and do some debugging, not that an update has ever broken anything.

There is some minor maintenance I run maybe once every 6-12 months to clear caches or fix up any configs that need updating but I've never run into anything that prevents booting.

[Tenoke]

Just Ubuntu though admittedly I use a lot more packages than average so there's more that can break across updates. Also a lot of things that have caused me problems over the years are getting more stable.

[qalmakka]

Ubuntu is famous for breaking spectacularly as soon as you start install PPAs or non-stock packages. I'm still convinced that APT is not the right tool for a desktop OS, it's way too complex and has too much automagic to withstand a user that wants stuff like the latest versions of GCC, etc.