have you tried printing from the command line? Sometimes when I run into printer problems, I open a shell and send something to the printer like:
echo test | lp
and see if I get any errors. If don't, I restart lpd and see if that gives me any errors. If the job spools to the spooler without problems, then your problem may be with the windows permissions set on the printer. I've used the printtool GUI a lot to set up my smb printers and experience the same thing, a jobs says its complete, but never leaves the spooler and never returns an error. Sometimes going to the command line will give you more of a clue as to where things are failing.