I am looking to outsource some server administration tasks. I need someone who I can contact on an as-needed basis and trust to get the job done right the first time. If you have any personal recommendations I'd love to hear about them. Or should I just hit a freelance site and test my luck?

Freelance sites are fine, just make sure they have good rep... you can usually pull off great deals on freelance sites.

Tons of people do this

try cliffsupport.com

Big talk for a 17 year old