Here's a shitty alternative that highlights the best points of your 
class-based suggestion:
##
def S(**kw): return kw
AppServer = S(
    Applictions = S(
           MyApp = S(
             Dirs = S(Products = '/home/tavis/Webware/Products'
                      Services = '/home/tavis/Webware/Services'
                      )
                    )
            )
    )
##

The syntax is only marginally better than plain dictionaries and you 
can't do cool things like:

##
class _SharedSettings:
    foo = 1234
    bar = 'aoeu'

class AppServer:
    class Applications:
        Class MyApp(_SharedSettings):
           ...
        Class OtherApp(_SharedSettings):
           ...
##

OR 


##
import os
class AppServer:
    class Applications:
        Class MyApp:
            if os.name == 'NT':
                ... settings for NT
            else:
                ... settings for Posix systems
##

and so on

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