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Using pydoc in the interpreter doesn't tickle any of these 
bugs, so hopefully I can narrow my focus down to the 
difference in handling between serve() and help(). 

Python 2.1 (#15, Apr 16 2001, 18:25:49) [MSC 32 bit 
(Intel)] on win32
Type "copyright", "credits" or "license" for more 
information.
>>> import pydoc
>>> pydoc.help

Welcome to Python 2.1!  This is the online help utility.
[...]

help> modules
Please wait a moment while I gather a list of all available 
modules...

[list of modules] 

Enter any module name to get more help.  Or, type "modules 
spam" to search for modules whose descriptions contain the 
word "spam".

help> DemonstratePydocBug.ReloadFails
Help on module DemonstratePydocBug.ReloadFails in 
DemonstratePydocBug:

NAME
    DemonstratePydocBug.ReloadFails

FILE
    c:\python21\lib\demonstratepydocbug\reloadfails.py
[...]

help> DemonstratePydocBug.TryThis
Help on module DemonstratePydocBug.TryThis in 
DemonstratePydocBug:

NAME
    DemonstratePydocBug.TryThis
[...]