My original site was written by hand in plain HTML back in 2001. It used server-side includes, repetitive style settings in each element.
I replaced that with a Zend Framework site when it first came out in 2006. It used PHP, CSS for stylesheets, had a MySQL database for storage.
In 2008, I got a very time-consuming job, and didn’t have much left over for making tweaks, so that was my first dive into a CMS. I picked Drupal. At the time it offered me all the tweaking I wanted, was fairly flexible, and didn’t require a lot of baby-sitting, or so I thought. Time marched on, my updates lagged, I ended up several versions behind the current release. So, do I spend a day bringing it current, or do I spend a day moving to something that I can keep updated easier?
Today I moved to WordPress. My “day-job” company moved to WordPress late last year, and it has made keeping that site up-to-date so much easier.
Here’s to the next few years.