This work is not blocked on the OEP proposal, and better yet, would help prove out what the proposal might be.
My hypothesis is that including dates in the comments would make it simpler to spot really outdated constraints.
What constraint removal do we want to task or not-task? For example, maybe Django upgrades don't need to be tasked, or maybe we have epic for future upgrade work?
We don't have to land all updates at once. We could iteratively improve this file. But, the sooner the better, so that others might copy/paste the patterns.
Consider adding additional README docs for what to do at the top of the file.
Once this work is done, consider ticketing the same work to update common_constraints.txt as well.
Improve the comments and tasking for constraints in https://github.com/openedx/edx-platform/blob/master/requirements/constraints.txt to make it simpler to track how and when constraints could be removed.