have you looked at the livecd-tools package?
https://projects.centos.org/trac/livecd/I use the tools to create a live CD that I can use to install a TSM client on for recoveries.
1/ that would be down the skills of the non skilled person and nothing to do with what was on the CD :-)
2/ this can be customised in the live cd tools using a kickstart file to create the options for you.
3,4/ you would have to write it, perhaps using `dialog` and that may well be a whole question in itself.
5/ you would certainly be able to ssh onto the system, reinstalling an O/S depends on how you want/need to do that.