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.
I’ve switched from my two three years old dedicated servers to one brand new virtual server. Reasons are : These servers costed me too much and they were becoming old (risk of failure increases). It wasn’t worth it. I spent last night doing that because I didn’t want to interrupt anybody using these servers. My two servers were running some Debian and I’m now switching to a CentOS virtual server. I was a little bit worried at first that CentOS would have a crappy package management system, but its yum is in fact working the same way as Debian’s apt-get and OpenSuse’s zypper.