FWIW I did finally get it working, to an extent.
I'm working on a Windows 7 machine to do this.
In one command tool window, I'm running my web2py application.
In another command tool window, I'm running the scheduler for my web2py application.
In the model that contains the scheduled task that gets called I placed the following two lines along with the import of rpdb2 elsewhere.
logger.debug('AWAITING DEBUGGER CONNECTION TO CONTINUE')
rpdb2.start_embedded_debugger("whatever")
Note that I comment these lines out when not needing the debugger.
I submit a job to the scheduled_task table.
When I see the 'AWAITING DEBUGGER CONNECTION TO CONTINUE' message in the scheduler command tool window, I go to yet another command tool and start winpdb and go through the attach.
This connects me to the proper process and I can step through it.
NOTE: You should change the timeout to the queue task call to something like 600 seconds so that web2py doesn't think the process took too long to run and reaps it while you're debugging.