Jason R. Coombs <jar...@jaraco.com> added the comment:

I like Nick's proposal. It has I believe the features that satisfy the 
use-cases of which I'm currently aware... with one edge case you may not have 
considered - support for multiple `__sitecustomize__` locations.

Consider, for example, the case where `__sitecustomize__` is in some system 
space unwritable by the user, but the package being installed is being 
installed in `--user` space.

Or consider the case where permissions aren't at play, but where you have a 
package installed in a different part of the PYTHONPATH. For example, [pip-run 
installs a sitecustomize 
module](https://github.com/jaraco/pip-run/blob/6203b1aa8cb52b5c181457054cf6ddaa40361437/pip_run/launch.py#L33-L44)
 in a temporary directory that it adds to sys.path. Ignoring for a moment the 
reason why it does this, I'd like to focus on the general need - that multiple 
paths on PYTHONPATH might expect `__sitecustomize__` support. You wouldn't want 
to have all of the `__sitecustomize__` hooks in one directory, because then 
they'll be decoupled from components that may or may not be in PYTHONPATH.

For these reasons, I think you'd want for `__sitecustomize__` to be supported 
to exist in multiple locations on PYTHONPATH and honor all of the files in all 
such directories, somewhat similar to how namespace packages are supported.

----------

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<https://bugs.python.org/issue33944>
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