The main obstacle right now in getting other people in to help maintain the site is collaboration. I've always just kept the entire site on my hard drive, edit pages in a text editor (GUI what?) and then FTP the modified pages to the site. This method doesn't work well when many people are editting the pages (I could merge the changes manually but that doesn't help free any time). Just about all CMSs would allow multiple users to edit pages but I really don't need all the extra fluff (which is mostly useless for this site) the systems offer.
What I really just need is a simple document management system that would let multiple users work on the site at the same time (either with an online editor or signing out and merging documents). I haven't found anything that fits the bill, though, but if someone has any ideas just drop me a note. I'm sure I could roll up a very simple PHP/SQL system that allows online editting but would rather use a free/open source alternative if there is one.
Of course, I'm still partially open to using a CMS system if someone can just sell me on it. I'll be continuing to play around with them to see if its possible.