I've hired this guy before:
http://www.supportm.com/
He's awesome and only cost $50/month.
I do have a server I manage myself. I did let some techguy set it up and install everything I needed and remove stuff I didn't need like FTP, Email and other stuff.
Changed MySQL and SSH standard ports and many other security-related things I dont remember.
I have automatic updates turned on and just login to Webmin once in a while to check if everything is OK.
So far no problems and it have been running for nearly a year now. But I wouldn't host any critical sites on this machine...