Hay there Neal, have you tried dosbox or any of the other dos emulators? With a bit of tweaking they can be set up to run most games. I regularly play a few games from the past. Just the other day I had Eye of the Beholder running, sure beats the pants off a lot of modern rpg’s.
Anyway, is does not sound like a HD problem. Seems to be having trouble with ram. You could try to disconnect the hard disk completely just to see if it makes a difference and to see how far it gets in the boot sequence.
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"Don't talk to me about naval tradition. It's nothing but rum, sodomy and the lash"
 
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