Steve Dower added the comment:

#2 should be fixed with the new installer (not necessarily the 3.5.0a/b/rc 
versions, but final 3.5.0->3.5.1 and upwards should be fine).

The problems with 3.4's installer seem to be largely due to the pip bootstrap 
being a critical part of uninstall. I've deliberately made the 3.5 uninstaller 
not fail if pip won't uninstall cleanly, which should allow upgrades to occur 
even if the previous install is corrupt.

Another workaround here is to go through Programs and Features, though 
sometimes it is possible for the entry to not appear. That should be fixed with 
3.5 (at least through the supported ways of installing it), but as I'm not 100% 
sure what causes the issue with earlier versions I can't guarantee it yet.

There's actually a sizable list of environment variables that could cause 
problems (PYTHONPATH, PYTHONHOME, etc.), worse on Windows because it's so much 
more common to have multiple versions installed and to set system-level 
environment variables. Maybe adding a "Compatibility Check" page to the 
installer could be handy? It could check these, maybe look for build tools or 
runtime dependencies and provide links or help for fixing/getting them. Another 
great idea, but not sure when I'll personally have the time to implement it :)

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<http://bugs.python.org/issue24873>
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