What's funny about this is that the whole idea of the "web of trust" was (and, as you demonstrate, is) literally PGP punting on this problem. That's how they talked about it at the time, in the 90s, when the concept was introduced! But now the precise mechanics of that punt have become a critically important PGP feature.

I don't think it punted as much as it never had that as an intended usage case.

I vaguely recall the PGP manuals talking about scenarios like a woman secretly communicating with her lover, or Bob introducing Carol to Alice, and people reading fingerprints over the phone. I don't think long trust chains and the use case of finding a trust path to some random software maintainer on the other side of the planet were part of the intended design.

I think to the extent the Web of Trust was supposed to work, it was assumed you'd have some familiarity with everyone along the chain, and work through it step by step. Alice would known Bob, who'd introduce his friend Carol, who'd introduce her friend Dave.