[chef] Advice sought on Chef-ifying heterogeneous mess of Unices

[Christopher DeMarco < >]

I run a smallish shop of about 50 Linux and OSX boxes, all of varying vintage.  All are one-offs, and all are SPOFs.  There are very few apps/configurations in common - MTA, SSH, some backup systems, etc.  

I tried Puppet ca. 2008, and ran into 2 problems, which I'd like to avoid with Chef:

1.  Where to start?  I began learning by putting my .emacs and .bashrc  everywhere.  While that was cute, it quickly became more trouble than it was worth, because I didn't automate anything of high risk, value or volume.

2.  How do I get legacy systems into the fold?  I have every version of Ubuntu and OSX since 2007, and therefore my Ruby will be archaic. 

I don't have the luxury of tearing down most systems to start anew, and we don't (yet) have a good testing infrastructure or protocol.  

FWIW, Vagrant was my gateway drug to Chef, so I have hope that I can at least use that to prototype/test services for cybernetic replacement.

What advice do you have for somebody trying to automate a shop like this?

Thanks in advance, and I'll see you at LISA!

--cmd

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Christopher DeMarco < "> >

+1-412-708-9660