I've got sort of a similar thing here:
http://members.iinet.net.au/~admurray/cgi-bin/faq/faq.pl
In the case of my site, it has only one or two steps to a solution; but it
can be built on.
I've used the scripts from
www.ezscripting.co.uk to build a database system
(the scripts read/search/write to a delimited text file (CSV) system).
Very basic, but does the job. Uses Perl/Cgi for Unix.
But while this is basic, I expect you want something like the "help and
support" troubleshooter(s) that Windows has - correct? (or am I assuming
this might be too advanced for your skill level?) It wouldn't be a quick and
easy way to implement what you want, but would be closer to exactly what
you're after.