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How are you planning your SCM monitoring roadmap?

I'm in the process of identifying checks I'd like to Audit on my application servers. Typically these are configured with Chef so I've thought of building a roadmap based on Chef Role validation, (Ex. .Net version,  TLS version checks). I also have been considering where I want a watchdog on files, like any edit to a web.config except for a certain deployment service.

What registry or file checks would you look for?

How are you creating a roadmap for your implementation?