For better or worse, you do trust people like this (assuming you're running a nonzero amount of Python, Ruby, Rust, or whatever else software).
> Say that to the 5444 PGP keys in the current web of trust that signs and maintains most packages for every major linux distribution running the bulk of the services on the internet. It works just fine.
That's tiny, and is exactly my point: these kinds of small rings of trust don't remotely resemble the trust topology in a free-for-all packaging ecosystem.
> "But look, everyone is negligent, and they are not likely to change" is not an excuse to not adopt obvious massive harm reduction with little effort.
This is not the argument being advanced. The argument is that we need to do better (in terms of misuse-resistance, etc.) than long-lived keys and the kinds of nerd-cred "get good" assumptions made in PGP-style webs of trust.
Nobody thinks that signing is bad; the problem is when you push the median developer to adopt it without any clear contingency plans for when, not if they fail to uphold the invariants you assume.