Because PyPI (or an attacker) could always substitute a new key. There's very little value in the signature and key coming from the same source: the key (and its justified identity) always need to come from a source of trust, not the source that's being verified.
> 99% of the time what I want out of package signing is to know that the new version of the package I'm downloading is from the same people as the old version. I don't actually need to know who those people are...just that they are the same people as before.
This might be a misunderstanding, but I don't think you actually want this: lots of large packages have multiple release managers (and contributors who come and go); you don't want to manually resolve each new human identity that appears for a package distribution.
What most people actually want is a strong cryptographic attestation that the package distribution came from the same source as the thing hosting the source code, since both that service and the owner of the repository are presumed trusted.
Notably, PGP is incapable of providing either of these: you only get key IDs, which are neither strong human identities nor a strong binding to a service. Key IDs might correspond to keys with email (or other identities) in them, but that's (1) not guaranteed, and (2) not a strong proof of identity (since anybody can claim any identity in a PGP key).