The Map of Chicago Magic is a side-project of mine. I started it in 2008, but after a couple of years of manually editing the Google Map, I had to give up on future updates as it become impossible to find, order, and maintain the data set. (A victim of its own success, in many ways.)
For more than a year now I've been working on extracting and cleaning the data so I could re-launch the site with a new, more sustainable approach. I don't have a lot of time to dedicate to this project, but I wanted to keep it living.
Recently, I finally reached the point where I was ready to begin authoring the re-imagined site. I was lured by static generators such as Webby, Django, Blogofile, and so on. I spent a good 20 hours or so researching and trying out countless versions of those type of tools. I also looked into using Wordpress or Moveable Type. Without getting specific, the problems I ran into ranged from seemingly abandoned projects, poor documentation, and frankly overly complex and obtuse approaches to relatively simple problems.
In the end I turned to using Tinderbox from Eastgate Systems. I've been using it for over a decade for my Usable Help blog, but honestly, I hadn't touched the code behind that for more than five years. My under-the-hood skills were rusty, and lots had changed since the last time I got into the details. But starting from scratch, and with just 3 or so hours of work, I had a functional prototype up and running. And when I decided to generate a KML file for use with Google Earth,it only took about 30 minutes to add that feature.
So while the lure of "something new or trendy" is strong, sometimes it's better to dust off a familiar tool and just get to work. There's a lot to be said for commercial, documented, and stable software when it comes to actually shipping something. Thanks, Eastgate.