Is there anything I can do?
hard to tell from here...
from the things you could do is try to do is: 1/ winedbg diablo 2/ then when winedbg seems to hang, try to attach gdb to it (to the winedbg process, not the diablo's as you did). it may tell us where it fails
another option is to run with --debugmsg +server,+relay but you will get lots of traces... but it may show where things stop
and the third one is to run gdb thru winedbg (run winedbg -- --gdb diablo, and see what gives)
A+