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Your problem sounds like the cupsd daemon may not be running. Usually "/etc/rc.d/rc.cups start".
Have you checked to see if you can still print from the Linux box recently?
Did the Linux box queue the job or was it stuck at the Win box? On your last attempt, the message would indicate it is stuck at the Win box.
With Win2K there could also be security issues, but if Samba is set to "share" level rather then "user" then it shouldn't be an issue. Except write permission to queue the file in the spool directory.
If you have file/printer sharing enabled in Win2K then there could be master browser issues. You could try shutting down both boxes and then starting the Linux box first, followed by the Win box. Samba has settings that can be increased to raise the level when a master browser is challenged.
Perhaps some of the above will help identify your problem area. I haven't used Samba for quite awhile, so I am not that familar with any of the new options or problems. But I used to run a Win2K box that used Samba share level OK for files and printing.
You might want to review the cups log files in /var/log/cups. (Edit: That may be the error_log you mentioned.) You can also see if cups will print a test page correctly. Uninstall the printer in cups and then reinstall perhaps.
If you still have the prior kernel you boot that and see if the devices change. If it was a default kernel, that can be reloaded from the CD. If you were running the default kernel before then the printer port was a module. I think the module was parport or lp. You could use lsmod and see if the module is loaded.