How can I be certain that my application is running on development server or not? I suppose I could check value of settings.DEBUG and assume if DEBUG
Typically I set a variable called environment and set it to "DEVELOPMENT", "STAGING" or "PRODUCTION". Within the settings file I can then add basic logic to change which settings are being used, based on environment.
EDIT: Additionally, you can simply use this logic to include different settings.py files that override the base settings. For example:
if environment == "DEBUG":
from debugsettings import *