Debian is, in my opinion, the best distribution for a server you have to maintain yourself.  That's because it takes care of a lot of stuff for you and apt-get is soooo easy to use.

Of course, you have to keep your server updated or, sooner or later, someone will hack it to itty bitty pieces.  And running updates automatically is dangerous as someone can mess with the DNS server you use and get you to download trojanned software nice and automatically - wonderful!

So instead of updating everything automatically, install apticron and it will automatically check what updates are available and it'll email you daily to let you know if something needs updating.

Then you can log in to your server, check that everything's OK and, if it is, do the update.  It's magical :)