Ok, so tsample.zip is a test case for the original problem, right? 
I can reproduce the problem on Linux also.

I can't make it crash (on Linux); what do have to do to make it crash?
If I access localhost:8080, I get log messages saying
2006-12-06 07:21:06,999 INFO servlet::__init__:1091 code 404, message File not found

eloff: this report actually reports two problems (the I/O error, and the crash).
Which of these are you having and have found lots of people having?

As for the traceback problem: this is due to the main thread terminating, and
therefore the logging atexit handler getting invoked, which closes the file.
Only then is the threading atexit handler invoked, which waits until all
non-daemon threads terminate.

As a work-around, add httpServer.join() at the end of your script.

I'll attach a patch that fixes this problem in the Python library.
File Added: threading.diff