(Been busy with other projects…)
This has been helpful, and has got me part of the way there.
However, (on my setup at least), there is still a huge show-stopper. Because the *user documents* directory, where TurboCAD looks for scripts on startup of the Ruby Console, is on the network, my initial file is *found* by TurboCAD but fails to load.
If I move it to another location, or explicitly load/execute it, the file loads fine and seems to find the required dependencies just fine (after adding the $LOAD_PATH << line), BUT the line to add a menu command does nothing. Hence, the scripts can't actually be executed.
This *may* be a peculiarity with my own particular setup (running Windows 7 inside a Parallels VM, and the user home directory is mapped as a network drive to my Mac's home directory), so I hope to test soon on the client's computers. But since everything else has behaved identically on their setup as to mine, I'm not overly hopeful of it working.