What kind of functionality do you need? I find that there are numerous plugins for what I want to do. Drupal is the next step up if you need total integration, but I haven't had the need for that yet.

I've started doing my sites with wordpress.. as of idk like two or three months ago. Just finished http://jitterzzkoffee.com/ which runs wordpress.

The key to working with wordpress.. in my opinion is to start w/ a basic theme, add what you need. Use existing plugins like a boss. There's really nothing complicated about it..

You just sorta make theme. Add pages.

ZZ is right, that's the best way to go. However I wouldn't always be afraid to start with an advanced theme, as long as the licencing permits you to edit it frantically.

In related news, I once tried using wordpress as a CMS, but whatever plugin I was using disappointed me, so I never bothered looking for a new one. Instead, I just setup the main site as a blog with static pages for other content.

Somewhat related: Drupal sucks. (It uses 60 queries per page, after caching, no plugins)

My current favorite CMS is cmsmadesimple; although it can be a little tricky to deal with plugins.

Speaking of themes... go wild with this one: http://www.plaintxt.org/#sandbox

This is Exactly what you should start w/ if your using wordpress.. And then if you want to extend functionality a bit just browse some others to find example code for doing random cool things. Proprietary themes are too generic/noncustom in my opinion. I prefer to start from the ground up. Or in this case.. as close to the ground as i can get without hurting myself.