I know nothing about managing a server so I'd have to pay to have it done.
It's really not that hard once it's setup; just run updates every so often via ssh... What is a pain in the butt is if you don't keep things updated (a lot of the time just normal user scripts installed on yoru site) you're responsible for cleaning up the mess...
I was managing 18 servers at the old webhost I used to work at (was let go due to "restructuring" unfortunately) on my own.
