I'm bootstrapped, and don't ever plan on outsourcing anything - except for maybe writing blog posts. But the feeling of needing to be close to a phone or Internet connection at all times in case of the inevitable really concerned me.
But then I sat back and breathed - downtime happens. It's not the end of the world, my customers will survive. I've recruited a close sysadmin friend of mine to be on call should anything ever happen, who I'll pay per incident. But that's it, life is too short to worry constantly and be glued to your phone while with your family or loved ones.