Come, come old chap. Only 24 years!
You are still a beginner
The whole reason for using the packaged versions of Asterisk is that it spares you from looking at those horrible gnomic settings.
I don't honestly know what idiot guides there are for AsteriskNow, I've never had real cause to test it. But if you want to look at Trixbox then I would heartily commend
Trixbox without Tears as the most comprehensive manual in any form.
The trick is to take one problem at a time and don't be afraid to reinstall when you really cock it up.
Get a couple of extensions operating, you can't do anything without that!
Connect to a VoIP service (or two) and work out how they work (they are all different to a greater or lesser degree). Even this has two stages- Inbound then outbound and you will find
Webmin and
Putty are invaluable tools to help sort out the network settings for this.
Then you can get big ideas and start confusing yourself with ISDN, FXO and FXS.
The Asterisk CLI is Asterisk's control screen and can be accessed from the server terminal, or preferably by a remote SSH terminal like Putty (You can scroll up and down), by typing asterisk -vvvr (the more v's you use the more comprehensive the information). It will (usually) tell you exactly where things stop working and in something approaching English.
If you are stuck, we usually ask for the config file entries because they are much easier to read here than on webpages we can't access.