(I haven't looked at Tangled at all. If Tangled has a secret management story for its PKI that's stronger than a private key on disk and can demonstrate that a non-trivial number of PyPI users would benefit from federation, then it's a strong candidate.)
PKI definitely is still hard, but if it can be done well by a smallish number of trusted parties to the benefit of their users, this can have huge ecosystem benefits. Let's hope we live in that timeline.