As a non-programmer, mostly designer and now web manager, I suggest people take a look at drupalgardens.com which is about to go into open-beta. Aquia is setting up a fairly painless way for beginners (and web devs who want to set up sites for small businesses, orgs and individuals) to dip their toes into the Drupal universe.
They are still working on the business model (free and premium accts. etc), but have developed a wonderful theming system, some basic installs (blog, product/service, campaign, etc.). They will upgrade the core and modules, are working on a basic set of contributed modules they'll support, and have a good Forum and also issue tracking set up.
They are developing an introduction to DrupalGardens which explains the main Drupal terminology, like content types and views (they have Simple Views, which of course doesn't do all that Views does, but is much simpler). There's still much to be done, but they are doing very well with it. For some sample sites, check out: http://sampler.drupalgardens.com/
It's a great introduction to Drupal and it will have much more flexibility than wordpress.com by the time it hits 1.0, imho.