I had never done any wiring beyond adding accessories until last year when I rewired under the hood of my '65 Coronet. I did post a thread for it which you can see on my profile but several of the photos didn't load.
It's actually not that difficult if you break it down into individual circuits such as starter circuit, charging circuit, ignition circuit, main power feeds, lighting harness and accessories such as w/s washer, horns, electric fan.
If you want to upgrade your electrical system I would wholeheartedly recommend reading everything on Mark Hamilton's MAD Electrical website and then deciding what you need to incorporate.
I did the MAD trunk mount, start'em up, new system, headlight and fan relays and ammeter bypass. The difference is significant.
I posted a wiring diagram on my thread.
I would suggest that you simply remove each wire one at a time and record them on a diagram. You will find that there will probably be redundant wires, duplicated wires and connections and splices all over the place.
When you remove the old wiring, you will have to figure out what the hell the previous owners were trying to achieve and this will increase you're understanding
You will also have to devise modifications if you have non stock parts or upgrades and this all helps to increase knowledge too.
On your new diagram, just add each circuit back in one at a time either stock or with upgraded mods.
Crimp, solder and heat shrink everything.
The cost on my Coronet was about $250 with all the MAD upgrades and cable. I have enough cable left over for my other Coronet which I have just started and it doesn't seem anywhere near as daunting, although I have sought advice on this forum because there were differences, but someone is always here to offer advice.
Good luck
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PS. Have a look at this!
http://www.forbbodiesonly.com/moparforum/vbpicgallery.php?do=big&p=11046