On my spare time, I manage a handful of servers. And even if it’s not really my job, I try to do it well and efficiently. All of them work on Debian because it’s simple to manage. I started using cron-apt a few years ago. I started by upgrading everything automatically, this was a big mistake. I switched to only sending mails on available upgrades and doing the upgrade manually. But this is also quite painful because 95% of the time, it consists in typing “apt-get dist-upgrade -y” and waiting and I have lots more interestings things to do.