[URGENT] Problems Booting from External HD

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I'm at a complete loss on this one. I'm a pretty competent Mac geek, and even I can't figure this out. Bear with me, I'll try and explain my problem as best I can. First, some basic info:

My hardware setup:
  • iMac G3 600MHz
  • 1GB RAM
  • 120GB internal HD, running OSX 10.4.7

The computer's internal drive is used by someone else for work during the day. I run all of my files and programs from a 2nd HD, which I boot from:
  • Seagate 300GB HD
  • Bytecc combo USB/Firewire drive enclosure

Software:
The only recent install I've done is Super Duper, which I did after I began having problems. I used it clone my Firewire boot drive to a (backup) 400GB external USB/Firewire drive, and I restored from the clone once when I began having the problems that now appear to have come back. At the time, it appeared that restoring from the clone had solved my problems. I'm fairly certain that my problems are software-related: I've installed the drive in question in another Mac (internally), S.M.A.R.T. status appears fine. I'm not using anything awful like Norton Disk Doctor, I've tried rebuilding the volume using DiskWarrior, without success.

Problem:
I am unable to boot from my Firewire drive. When I start up using it, everything appears normal, until I get to the boot panel. The progress bar loads very slowly, and only gets about halfway finished before the login panel appears on top of it (even though the boot drive is a single-user volume, set to login automatically). The username and password fields are both blank, and if I enter my username and password it says it's incorrect.

Symptoms
  • OSX/programs become unresponsive after waking from sleep. Computer freezes, and most recently the screen went completely gray. After forceably turning off the computer and HD and restarting, I get the problem I just mentioned with the login panel. I don't have any problems waking from sleep if I'm booting from the computer's internal HD.
  • Certain programs (notably iTunes and Adobe CS2 apps) periodically become unresponsive and quit. Several times I've gotten an "unknown error" message from iTunes saying that it is "unable to save the iTunes library". Both of these issues usually precede the main problem of being unable to boot/login.
  • Occasionally, if I boot from the computer's internal HD and then switch on the external, it refuses to recognize it as being a formatted OSX extended (journaled) volume. Turning it off for several minutes and then turning it back on sometimes fixes it, as does repairing it using Disk Utility.

These problems have been plaguing me for months now, and with more than one external HD (although using the same enclosure). Everytime I do something to fix it, the problems seem to go away for an increasingly shorter amount of time, before reappearing, each time slightly worse than before. I'm convinced all of the issues I've been having are in some way related, I just can't figure out how they're related (or what I can do to fix them). Hopefully, one of you can help me. :)
 
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