Per https://github.com/docker/docker-py/blob/master/requirements.txt: It looks like there's no longer a requirement to depend on older versions of dev-python/requests. Removes quite a few blockers between this and other ebuilds.
Yep, looks like the latest release does indeed lift this restriction finally. I'll be bumping tomorrow and getting into the tree by next week. I'll update this bug as I make progress.
This is fixed as best as it could. Please reopen if you think this is still an issue.