Some of the fingerprinting involves not the user-controlled configuration of the machine, but hardware-related aspects like the canvas fingerprinting which looks at pixel level details of a small rendered figure. That combined with IP address will go a long way.

"Logging in to the Guest account on OSX accomplishes what you want, no?"

No ...

That is, unless I can easily script the destruction and recreation of the guest account, and automated install and configuration of my chrome setup ...

The idea here is that I set up chrome just how I want it and deploy and redeploy that "container" over and over - destroying it and recreating it after each use. Possibly with multiple instances running simultaneously ...

When a Guest logs out, any files they created are destroyed, including cookies and browser histories. But I don't know of a way to have multiple instances running sumultaneously.