Looks like you get a ticket trying to display the application error ticket. I had that once but I was debugging something in trunk that was broken at the time.
You mentioned you have a fully and properly working debain version. I believe it is legit to move the files under errors in your application to the system that works and look at them there using the admin interface. That might help get a handle on it. Also when the admin system gets an error you will find the ticket file under applications/admin/errors. You are using stable from web2py currently 1.95.1? I would be tempted to download the zip file, unpack it and slide it into place where the existing one is now after you rename the top directory of the old one. Then you can run a diff to see if something got changed somehow. Is there a requirement to run GAE on python 2.5? What version of Python is on your debian system where everything is working? I run standalone or under apache with wsgi on Python 2.6.5 without issues. Have a look at web2py/scripts/setup-web2py-ubuntu.sh and you can see the packages that get loaded in there. I wouldn't load in matplotlib or reportlab unless you need them. Ron