How can I resolve this python and django settings import idiosyncrasy?
No. Use from ... import * or execfile() in settings/__init__.py to load the appropriate files.
I have a file layout like this:
settings/
----__init__.py
----common.py
----configs/
--------constants1.py
--------constants2.py
----debug/
--------include1&2.py
--------include1.py
--------include2.py 
and when I import settings.debug.include1, I would like the settings file to execute/import common.py then override the settings in common.py with the proper constants file. Problem is, this isn't happening. Is there a way to accomplish my goals in this fashion?