> 1#
class Food(db.Model):
    category = db.StringListProperty()
    [other properties]

apple = Food(category=['fruit','red','iron','apple'])
greenfruit = Food(category=['fruit','green'])
veg3 = Food(category=
['vegetable','category1','category2','category3'])

If you query category='fruit', you'll get both apple and greenfruit.

> 2#
Try to use auto-completion provided by some Ajax libraries like YUI.

> 3#
Do you mean XMPP and Jaiku, see 
http://morethanseven.net/2009/02/21/example-using-xmpp-app-engine-imified/


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