When I decided to blog my crestar site, over 2,000 html pages I wanted to convert to a blog or cms, I looked at all of the cms and blogs available via cpanel at my web host.
Many of them, not WP, had the lousiest documentation I've ever read. And I'm acomputer tech for the past 20 years, albeit with no php experience.
Some of them I looked at, not WP, had the exact add-ons, etc. I felt I needed. Then I saw they wanted 50 dollars or more for those add-ons. Or the add-ons, not for WP, didn't work with any version available.
So I went with WordPress.
A decision made easy by the other blogs and cms out there.
edit: well, I don't think all of those static pages on my site will fit into the blog format.
But that still leaves, as I find time to work on it, adding around 500 pages to be done.
It would be great if wp-dtree categories listing worked with wp2.3. That would certainly help me with certain headaches.