Gerry McGovern nails it in his new post Technology is neither magical nor neutral. He describes how buying technology, like a new Content Management System, isn't the answer to your business problems. Sticking your new content into a new system won't magically make it better or easier to understand by your customers; it takes careful management to get the most out of it. Well worth a read.
Gerry McGovern talks about why organisations hate their content management systems.
The main issue it seems is that people don't understand what they need their content management tools to do. And this is only exacerbated when most tools fail to provide even the minimum functionality:
a great many content management systems have extremely poor review and deletion processes... a typical CMS is like a digestive system with no capacity to poop
Smashing Magazine have a handy step-by-step guide to best practises for moving a Wordpress site. It covers moving from a local development site, a sub-domain and another host.
The CMS Files: Deane Barker has collected eleven years of his postings about content management systems. Lots of insight in there.
Kirby, a file-based CMS, looks like a decent option for small sites.