We have to distribute and maintain a somewhat complex software application, whose installer does not (nor is expected to) install and configure every part needed on any possible kind of server.
I've been the person responsible for the installation so far and I have knowledge of all the many pitfalls and tricks to get the installation to run smoothly. Now we have more people we want to train in this procedure and hopefully minimize my need to hand hold them while they're learning.
Thing is, a linear document for all possible cases would be far from ideal, because there are many possible paths in the process, depending on the starting point (Windows Server 2003 32/64 bits, Windows Server 2008 32/64 bits, SQL Server 2005 32/64 bits, Windows XP Pro SP2/SP3, .NET 2.0 SP1/SP2) and on all the possible problems that arise in each combination.
So, I'm looking for a tool that is designed with this scenario in mind, hopefully generating documentation based on a set of input parameters (configuration of the machines) or, even better, a tool that will guide the installation process based on what's been happening and which can record new problems and map them to known solutions.
I can envision writing such a tool, but it doesn't look like a (very) trivial problem. This seems to be the intersection of a knowledge base and an expert system.
So, what do you do? Assume defeat and have huge linear docs and FAQ like KBs?