I received a lot of positive feedback on my last post, and some of the ideas posted on the sites that picked it up gave me the inspiration to write this follow up. There were some good ideas and some questions posed so I thought I'd try to make few addenda and clarifications.
Choice of toolchain.
I chose OpenSCAD mostly as the first thing that popped into my head. The nightly version (2014.03 as I write), is fairly stable. The output it generated was well received by most of the other tools I used it with, which included Blender3D, for rendering the preview images, MeshLab for debugging the geometry when I goofed something, and LibreCAD for loading the 2D DXF files to send to my laser cutter. I even used Elmer to do some rudimentary(and probably naive) stress sanity checks.
I did lament that some the really cool features in the bleeding edge version of OpenSCAD were not available, but the generated output of the newer version had some erroneous geometry. I've read on the OpenSCAD forums there may be some versions for download that don't have those bugs.
I had worked with OpenSCAD before, so I knew what it's capabilities and limitations were. I wasn't really tied to OpenSCAD, here are some alternative tools work very similarly. Ultimately, it came down to the devil I knew, and that it supported all of the features that were critical to me: easy to setup, mature and stable, bug free STL and DXF output, and allowing me to programmatically override the skeleton designs by emitting generated design code.