This craziness (w.r.t. the winpdb install) is fixed with the following
patch to debhelper, but maybe the default should be changed upstream in
Python.

In a nutshell, there's a timestamp comparison going on (in the absence
of a contents comparison). If the dest is newer than the source, no copy
happens.
>From d767992775c45875912d2d7a55f6bba2a43c968a Mon Sep 17 00:00:00 2001
From: Andrew Straw <straw...@astraw.com>
Date: Sat, 26 Sep 2009 17:26:01 -0700
Subject: [PATCH] Pass --force option to Python distutils install command.

This command will prevent distutils from attempting to determine
whether a file should be installed based on the timestamp of the
to-be-overwritten file.
---
 Debian/Debhelper/Buildsystem/python_distutils.pm |    1 +
 1 files changed, 1 insertions(+), 0 deletions(-)

diff --git a/Debian/Debhelper/Buildsystem/python_distutils.pm b/Debian/Debhelper/Buildsystem/python_distutils.pm
index bc6e71f..1744004 100644
--- a/Debian/Debhelper/Buildsystem/python_distutils.pm
+++ b/Debian/Debhelper/Buildsystem/python_distutils.pm
@@ -167,6 +167,7 @@ sub install {
 	my $this=shift;
 	my $destdir=shift;
 	$this->setup_py("install",
+                "--force",
 		"--root=$destdir",
 		"--no-compile",
 		"-O0",
-- 
1.6.2.1

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