Therein lies the fun, if this is something that is not fun for others then I would say that Penetration Testing and or anything computer security related is not what that person should be involved with. Critical thinking is just one of those industry terms that comes to mind.
As for answers or documentation, the OP is correct that not all tactics, techniques or procedures have documentation that is relevant to the newcomer, and well it's probably better that way. Some tools do not even need documentation. I mean some tools are so simple in what they do it would not really be worth the effort to document it.
A simple execution of a command would generally be enough to figure things out. Then again other tools do need better documentation and do not have it.
Most tool creators would probably not mind if someone would actually take the time to do some testing and document the results.



