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.