Since my first WordPress site in 2008, I think WP has gotten much easier. You no longer need to FTP your theme files or plugins, and WordPress & some 3rd-party themes have made many things easier. And I agree that the WordPress codex has loads of info for the DIYer, but it's intimidating to most. Contextual help has helped a lot. But for many setting up a WordPress site from scratch can still be a challenge, but the results I have seen - moving a site from Blogger to WP or from HTML to WP...the results in look and feel and in traffic increases can be stunning.

I use a similar, but extended analogy to describe WordPress.

I use the analogy of WordPress being the free software that runs your website - it's like the car's engine. The Theme is like the make and model of the car - the look and feel of the website. Plugins are like a car's options - things you choose that make the website/car run and look better. Although I also like the analogy above of plugins and widgets as apps that add functionality.

For larger sites full customization makes sense. For the most basic of blogs - Wordpress's own three free themes (2010, 2012, & 2013) often make the most sense - they are simple and work pretty well out of the box. But for most smaller, simpler small business websites or blogs, a less than $100 premium theme often is the best choice. It actually often simplifies the process, and most often has security, basic SEO and a few other things built-in already. Something like Studio Press & the Genesis Framework with a child theme, or Woo Themes (there are others we could debate).

I know mentioning premium themes and favs may start another whole controversy here, but I like setting up my customers with a theme I am confident will keep pace with Wordpress's changes. Too many free themes leave clients left behind with an older, stagnant site, unable to take advantages of new features and updates.

I agree with Bob S. above, until WordPress includes a how to step-by-step tutorial, that shows up on the dashboard when you start a new site (and they are getting close). We need to step up and teach our customers what they need to know. It's easy to vet a plugin before use (check details, reviews, # downloads, recent updates, vetted for your version of WP) - do a search engine search for best plugins to do "X" etc. Teach them about site back ups & basic SEO. Make them as self-sufficient as possible is my mantra