NOTE: I know there are already tons of posts/threads on the WF about this topic. I'm not posting an "HTML vs. Wordpress" post here.
My point is this:
I've been doing my own websites for a long, long time. I'm not a "great designer" but I did learn HTML early on and made sites by hand, so I know more than just the what-you-see-is-what-you-get interface. Despite that, I've never made "pretty" sites, just functional ones that at least looked decent and not like they were made in 1999 or by a 5th grader in an hour.
Since last December in 2008, I was really starting to look seriously at Wordpress - and my main reason was I was increasingly building larger and larger sites - setting up and maintaining proper navigational structure can really be a pain in a ~100 page site.
I've been working with Wordpress now in earnest for some months, and recently started a new site after doing my keyword research.
Wordpress has made creating this site a breeze:
*Selected a nice, SEOd theme not requiring major code tweaking (minor tweaks)
*Installed a bunch of great, time saving plugins
*Navigation - via Category set up - a total breeze
*Page / post creation and updating, a total breeze.
*Insertion of graphics or videos? push a button or two.
*If I decide to change the total look of my site, it's as easy as uploading a new theme. Changed my mind? Push a button and reactivate the old theme. Easy!
My new site is MUCH better looking than I could have designed in Dreamweaver, was put together much more quickly, is more easily customized and updated, and Wordpress - being essentially blog software - pings for me and I can add a ping list too, so that's nice too. The variety of plugins helps to make my site very easily managed. If I want, I could install a relatively inexpensive membership plugin down the line to create a membership site, or just password protect parts of the site for downloads etc.
Lots of benefits, no real trade-offs. Sure, there's some risks in Wordpress - site can get hacked etc., but I'll look into site protection and plus, if you back up your site you can't lose anyway.
All in all, a dramatic improvement over doing sites in Dreamweaver - at least for me.
I don't mind if people want to bash or compliment Dreamweaver or Wordpress or even another CMS (Drupal, etc.) - I have no agenda here - this post is just in case someone is considering which route to go, I say go with Wordpress.
Hope that helps someone!