So, I've successfully used Vagrant and Chef to install an MSI onto a Windows guest VM. Woot! Then, I wrote a few tests with ServerSpec that check that after the MSI was installed, files got put into their proper places and things like that.
My question is: What sort of goals should I have when it comes to acceptance testing an install of a package like that? Should I be checking for specific files? But what if there are lots of files? Or is checking for each file too low-level? Too close to the implementation details? What level should I be at when writing acceptance tests for a successful package install?