man & info
This is too complicated to pull off, IMO. I get your idea but I've been working with Linux/Unix for the better part of 30+ years and continue to learn things every day that leave me wondering how I hadn't learned this bit yet.
I will leave you with this though. Most of the help that one requires on Linux/Unix is already contained within the system. The man pages and info pages are pretty much the owners manual to your system.
These commands will get you started:
$ man man
$ man -a intro
$ man -k <some topic>
$ man <command>
$ info <command>
Most people don't realize that you can learn about how the man pages are organized through the use of man. Try
man man to gain more insight into how they're laid out.
The standard sections of the manual include:
1 User Commands
2 System Calls
3 C Library Functions
4 Devices and Special Files
5 File Formats and Conventions
6 Games et. Al.
8 System Administration tools and Daemons
So if you have questions about commands, focus on the man pages in section 1. If you have questions about the file format conventions, look to section 5.
$ man -S ls
I kind of backed into Koans through Ruby where I first learned about them. They are snippets of a problem that teach you a concept in X.
excerpt from wikipedia
A kōan (公案?)/ˈkoʊ.ɑːn/; Chinese: 公案; pinyin: gōng'àn; Korean: 공안
(kong'an); Vietnamese: công án) is a story, dialogue, question, or
statement, which is used in Zen-practice to provoke the "great doubt",
and test a student's progress in Zen practice.
In my case it was with the programming language Ruby, but Unix also has them.
The ones that I'm most familiar with for Unix are the ones known as Rootless Root. Poking around that site you'll likely find these koans titled: The Unix Power Classic: A book about the Unix Way and its power. If you want to gain an understanding for Unix I suggest you read them.
You can often find documentation on the various software installed on a Linux system under this directory,
/usr/share/doc. This is at least the case on Red Hat systems, not sure about other distros. You can browse this info using a terminal browser or a web browser like so:
$ lynx file:///usr/share/doc