Sounds as though we need a decision tree app to write the scripts for us. It asks questions such as, "Do you have your own IP block?" and explains the question thoroughly for those who don't understand it, explains the answers offered (for questions such as, "Which of the following types of logins would you like to allow (check all that apply)? Password, public key, ...").

It would offer you explanations, deeper explanations, defaults, recommendations for when you would override the defaults, etc. for each item. It would be smart enough to prevent incompatible or contradictory settings.

Once this process was complete, it would generate the needed puppet / ansible / whatever script, which the admin would run and store for future reference and use. When installing another machine, the original script could be read in by the decision tree and the new script could be generated by modifying the original rather than starting from scratch.

I would start with Ubuntu 12.04 LTS on Linode and see what develops from there.