It's a steep learning curve, but Chef is totally worth learning if you want to automate ops. Use the time you're wasting on ops to learn Chef instead. If your outsourced ops guy is worth his money, he's probably going to use Chef anyway.

This. And if you don't want to go to the length of maintaining your own Chef server you can opt for hosted Chef:

http://www.opscode.com/hosted-chef/

Or puppet, which I prefer