I were going to proceed with the update, I'd opt for setting up a secondary
repository (osgeo4w-setup has an option -s to point to a different rep for
testing - not sure about apt).

I've setup a mirror at http://o4w-mirror.dreamhosters.com/repository/

At present it's a dumb mirror, meaning we can't use the server to calculate the md5sums and regenerate the setup.ini file. This could be changed but as I'm not familiar with how that works it could take awhile.

I don't have any bandwidth or space limitations on this server, but there is a conceptual one, it's not "mine", so this can't be a long term solution. This also means I can't add user accounts for package maintainers.

apt has a --mirror=... switch that works, though there have been some wrinkles with it which I'm not sure have been ironed out yet.

We could then put the new python there and start migrating the rest - without
any disturbance to the main repository.  Once we're content with the new
repository, we just need to move the new packages to the original repository...

python2.7 package is in the ./release/python directory and I manually patched setup.ini to use it.

-matt
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