Hi John,
I’m a relative newbie here an I agree with you that the User Guide isn’t the best!. However, I bought EE about 3 or 4 weeks ago and I highly recommend this set of tutorial videos:
http://mijingo.com/screencasts/learning-expressionengine-2-complete-series
It costs $48 for the lot which is more than worth it considering how useful they are! They cover a wide range of the basics and some of the not-so-basics. It should keep you busy for a solid month (like me!).
I have quickly learnt that there are some very useful plugins and modules that will save you having to do much custom coding at all. There are powerful (and paid for) ones like Assets, Matrix, Wygwam, Playa, CE Image but also loads of very good free ones (I like MX_Jumper, AJAX Detect, Shortee, Super Geekery Tag Stripper, Tweetline, cpb Garnish - to name but a few). Don’t worry about knowing what each of those do, just ask here at the forums when you have a question and someone will answer very quickly (usually within a few hours at the most). I am only now beginning to hit issues where I need to ask certain questions on these forums after a month of solid use.
It’s weird for me to come from a life of Open Source to an often paid-for community of tools, but to be fair, I make enough as a developer to cover these minor costs. And my clients don’t even blink at paying $50 to buy something that saves them a week of my time.
😊