Yes, I think whoever ends up taking over Python 2 maintenance would be well advised to stub out the https support immediately, and maybe a bit later do the same

Yes, I think whoever ends up taking over Python 2 maintenance would be well advised to stub out the https support immediately, and maybe a bit later do the same for all support for network requests. In particular, you don't want to have to worry about building against openssl. I think the vast majority of cases where people have a good reason to carry on using Python 2 won't need that.