I talked this over with Steve Dower, the current "platform expert" for Windows.  As he points out: the 3.4 Windows build is effectively unsupported.  The Windows platform expert for Python 3.4 resigned from core Python development.  Also, of course, all future Python 3.4 releases will be source releases only.  In short: if you make this change, you'd probably be the only person who would test it before it goes out the door.

But!  We still have Windows buildbots that can build Python 3.4.  And, since you're using a version of OpenSSL that we have checked in (on svn.python.org), it is theoretically possible to run this build on the buildbots.

So!  My price is: since you're going to have to coordinate with someone with the commit bit for this, you (and they) need to get this to pass on a Python buildbot.  Create a server-side clone, check in the change, and kick off a custom build.  When you get it working, post the results here, and after that you'll have my blessing to check this in to 3.4.