I recently converted more than 500 pages of static html into WordPress, and my site is more CMS than blog. The conversion from blog WordPress to CMS WordPress was helped by the amazing upgrade to v1.5 with the Pages feature and other improvements in template files, template tags, and plugins.
I document much of the move (I'm still adding articles as it was seriously intense and lasted for months) in the Learn > WordPress section of my site, but I have to say that life got a LOT LOT LOT LOT (did I say a LOT yet?) easier with the release of the following plugins that completely changed how I administrated the site.
Coldforged's Paged Comment Editing
Coldforged's Enhanced Admin Manage Posts Views
Warning: Because I am so in love with these plugins and totally worship their authors, the following will sound like a flaming endorsement and advertisement. Guess what - it is! And this is advertising for a FREE PRODUCT (donations welcome, I'm sure).
The first one allows me to have an amazing form of control over viewing my comments, including the ability to see the spam that is caught so I can delete it from my database, saving space. And see what is coming in so I can even take steps to stop it before it comes in the door. Normally, version 1.5 grabs the spam and you never see it, but it still sits in your database as a reference. Try this and you will totally love it.
The third one is TextControl and it allows me to set the formatting controls that WordPress automatically slams down on my content. Since all of my "old" articles were in static HTML, I wanted them to remain in the HTML tags since I had all the CSS and everything in them for a reason. TextControl allows me to set the formatting choices for every post (must click SAVE and CONTINUE EDITING to see it, though) so I can stop it from changing things in a way I don't like, or leave it to format itself the WordPress way for the new articles I write that barely have any HTML coding in them. It's brilliant once you understand the basics.
The middle plugin is the one that I greatfully thank the stars, gods, mother earth, first fire builders, and all the rest of the powers-that-be for. The enhanced view of the Manage Posts screen is amazing. I can sort posts by category, author, or date. Being limited by only date before, and not working with dates in a CMS format, finding posts or categories was near impossible. HATED IT. Time consuming and ridiculous. Too limiting. The Enhanced View Plugin makes life so easy to manage all the articles, I adore it. I use it constantly to see what I've posted where, and when, and edit specific series (categories) of articles all together. Totally and completely brilliant. You can also break through the 15 post list barrier and tell it to list as many posts as you want to see. I often set it to 25 or 50 so I can see ALL of the posts within a category. Did I say I adore this plugin yet?
The only other plugin (actually non-plugin but could be soon) that helps me to emulate the CMS functions that I need is called Batch Categories. Podz is supposed to be cleaning it up for re-release, last I heard, since it is rather challenging to install for 1.5 as it was written for 1.2. Batch Categories allows administrators to move posts between categories en mass rather than through the Post Edit screen. I can move 50 posts within a minute or two. Amazing. Very power hungry, but how often do you have to move a bunch of posts around from one category to another? When you farkle up your site by screwing with category IDs and Names....hey, it happens.
I believe in the right tool for the right job, and there are a lot of decent CMS programs out there, but my research last year overwhelmed me. Many had horrid looking interfaces with little documentation, or were so feature heavy that I felt like my site weighed a ton of bricks. It's actually a very simple looking site, and I wanted to lighten my admin load. WordPress isn't easy to force into CMS but it is growing in that direction and these plugins are a tremendous step in the right direction.
After that, you just have to deal with the chronological issue, but I think I've handled that well with Adhesive and stick plugins, and learning about how to control the WordPress Loop, the biggest challenge of all.