It occurs to me that if creating a cross-distro free replacement
repository is realistic, a better target might be addons.mozilla.org

Firefox and Thunderbird addons are used more frequently and by
non-developers, Trisquel is already attempting to maintain a free
replacement[1] manually, and the issue of non-free addons is also a
problem for all FSDG distros.

From this page[2] it appears that, unlike PyPI, Mozilla requires a
license statement and provides a clearly defined set of options:

Mozilla Public License, version 2.0
GNU General Public License, version 2.0
GNU General Public License, version 3.0
GNU Lesser General Public License, version 2.1
GNU Lesser General Public License, version 3.1
MIT/X11 License
BSD License
All Rights Reserved
Other

Apart from "All Rights Reserved" and "Other" all of these licenses are
free under the FSDG (and GPL-compatible), so automatic filtering should
be much more realistic. Anything labeled "Other" would have to be
rejected, and this would probably mean leaving out some free software,
but surely not as much as what gets left out by Trisquel's manual
approach.

[1] https://trisquel.info/en/browser
[2] 
https://developer.mozilla.org/en-US/docs/Mozilla/Add-ons/Distribution/Submitting_an_add-on

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