Need to develop a web site generation program that is simple

My brother's web site for his company, Cannon Custom Leather (if you need any leather goods made, especially for horses or dogs, give him a ring; obviously I am biased but his stuff is high quality and he really cares about what he makes), is now up. He used Publisher to make it which has led to decent looking pages considering my brother is not a computer person, but the page sizes are huge.

So, being the technically inclined brother I am, I plan to develop a web generation/publication program for him. The requirements that it be dead-simple for editing and creating web pages and that he be able to automate uploading files. Basically he needs to be able to maintain the entire web site on his own without me being a bottleneck beyond implementing custom features in the software.

I originally thought of using rest2web (actually used it in an initial version of the site that was used for a very short period of time), but I want simpler and to be geared more towards non-programmers. I also thought of Django, but I don't know how I would push all of Django to my brother easily for auto-generating a site. I guess I could maintain an install somewhere like TextDrive (been thinking about signing up anyway for a redo of my personal site and to get a remote svn repository for myself) and then do the sites that way, but I am not in the mood to have to maintain the server and email accounts and everything else that would go along with hosting my brother's site somewhere where I have a Django install. Plus, with his Yahoo! hosting he get PayPal and credit card purchase handling and eventually online purchases which is something else I could live without.

My current thinking is something really simple where the first line of a text file you specify the type ("index", "gallery", etc.). Then, following that, simple "variable=argument" pairings based on the type. And then, after a visual separator (like one or more dashes) the body. This allows for dispatching on the type to process the arguments and body (and thus allowing for straight-forward formatting of data in the body based on what type of document it is). Then all of this can be processed and past to a template (using what templating system I don't know) and then generate an XHTML page and other needed files (like thumbnails and such if I go that far).

Once the local copy is happy, then running another script will upload via FTP to the site. Probably will keep around a file that has the last upload time so that it can just traverse the web site directory and upload all files older than that.

Anyway, that is my current thinking on all of that.