This isn't necessarily comfortable advice to hear, but...forget the debugger. I've been dealing with python for six or seven years and haven't missed it. I'm not sure what the norm is for python developers, but personally, I don't think I've spent more than an hour of my life inside pdb.
On the flip side, get used to the interactive prompt. It's definitely the best way to get a feel for what's really going on. Pythons intropsective nature let's you dig into every nook and cranny. On the other hand, it would be really nice to have some sort of hook for dropping the cherrypy server into a debug prompt. Under development mode, it would be nice to drop to pdb instead of exiting because the auto reload picked up a syntax error or something silly....
