The other option is to find a host that specializes in hosting drupal sites and is willing to take care of all that for you. The biggest problem with this is that you can only use the features they install for you. Of course, they will also charge more than generic hosting, but it's still cheaper than getting a SysAdmin.
You could maybe offer to pay for (some of) the help with a sponsored link on your site. That could be reasonably attractive to a Chicago-based contractor with a low pipeline.
ahem
Is anyone a Drupal/apache shark and willing to help me tune my site and migrate to Slicehost?
We were featured on the HuffingtonPost, the Freakonomics blog, Playboy.com and numerous other "name" sites last week. Would be happy to discuss price or a link.