Here is my humble suggestion to improve Webwork installs after a lot of heartache and thinking about it. Comments welcomed...
(Probably the most ideal Webwork installation method would be deb and rpm packages. That would take a lot of testing and maintenance work. In the meantime.....)
To help professors with the huge installation TODO list, it seems it would be an improvement to provide a script that automated all the steps. If necessary, it could even pause before each command and ask for confirmation before executing it. It could also print chatty explanations of what is happening and why.
Humans just aren't as good as computers at lengthy tasks with lots of syntax.
I'm sure the Webwork wizards would welcome less emails about installation issues.
I've posted something in Python I'm working on. Jason A. has his own installation scripts. I'm sure others have their own as well.
Few would perhaps be willing to use some random user's scripts. However, if there was an official install script that had been blessed by the wizards of Webwork and linked to on the documentation server, that would make people trust it more.
This would have the added benefit that if everyone was using the SAME install script, it would be continually improved and made more robust with wider use.
If someone was having bad luck getting Webwork installed, there would always be the fallback option of simply creating a clean standard Ubuntu 12.04 LTS machine and running the install script before doing anything else. That would probably work in 99% of cases.
Just my $0.02.