I think the wsgiref issue was that it wasn't in site-packages and so couldn't be removed or upgraded. Having the dist-info available and putting them in site-packages (or a new directory?) lets us handle querying/replacing/removing using the existing tools we use for distribution.
Also, I think the version numbers do need to be independent of Python version in case nothing changes between releases. If you develop something using statistics==3.7, but statistics==3.6 is identical, how do you know you can put the lower constraint? Alternatively, if it's statistics==1.0 in both, people won't assume it has anything to do with the Python version.
The tricky part here is when everything is in the one repo and everyone implicitly uses the latest version for development, you get the reproducibility issues Barry mentioned earlier. If they're separate and most people have pinned versions, that goes away.
Top-posted from my Windows Phone