@pswenson, I used Chef to automate setting up the server with Jenkins. This included automated security updates, awscli tools, nodejs, and even hubot so that we can trigger builds from HipChat (we still need to write a custom hubot listener to handle that, though).

I also took advantage of AWS IAM roles so that the server is pre-authenticated for certain S3 buckets.

PM me at josh dot padnick at gmail /period/ com with some background on what you're trying to do and I'll see what I can share. For many reasons, I can't make our Chef code repo public, but maybe I can share some code samples.

Edit: Regarding Chef, for more info you might check out http://www.slideshare.net/JoshPadnick/introduction-to-chef-a....

As far as online examples, yeah, the learning curve does kind of suck. Also, if you're starting from scratch, SaltStack may very well be a superior technology (don't know enough about it). I think the key with Chef is to learn how to read the docs, using the application-cookbook pattern (where you never touch the cookbooks you download online and instead customize them by "wrapping" them with your own custom-defined cookbooks.

It's also helpful to use very thinly designed roles, and define special cookbooks as your actual roles. This way you can version-control them.

I basically learned by reading the same material in multiple places, especially in books on Safari Books Online, and IRC was also a huge help b/c the community was VERY helpful.

I think Chef is a classic case of where the technology is somewhat inelegant and perhaps bloated, but a mature community is there and it's battle-tested so once you suffer the pain of ramp-up you get a huge benefit.

HTH