As I reported in my earlier posting, I found a workaround for using MacPorts on a case-insensitive filesystem. After numerous attempts to figure out how to get an image to auto-mount cleanly, I decided enough is enough. I tried everything, including AppleScript and Automator. Great stuff, but the same scripts that worked when I would launch them manually failed to work properly when I tried to “open at login” on the dock. Needless to say, those technologies seem kind of half-baked to me.
So I decided to do a full backup of my system (using Time Machine) and reinstalled the OS, this time making sure my boot volume has the proper filesystem (HFS+, Case Sensitive, Journaled). Make sure you run Disk Utility from the DVD before beginning the install process.
You have two choices when doing an restore from Time Machine. You can do it after the install completes (and before creating your first user) or after installation using the Migration Assistant (in Applications -> Utilities). If you go with the latter option, I suggest creating a different username so you can use the same username as you had before (assuming you want it).
Anyway, I don’t think too many people have been glued to their computers wanting to know how this turned out, but I have decided to fix the problem permanently for my own sanity.
The lowdown: If you are serious about doing software development on your Mac, you want case sensitivity in your filesystem. Or at least make sure /opt lives on a case-sensitive volume that mounts at boot time.