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Could the squatter extort a fee from a large hypothetical user, say "McDonald's", that was lower than the bond necessary to overbid the squatter? (Off-chain or unofficially through back-channels).

Probably not a big problem for entities smaller than corporations, but maybe people like PewDiePie?

My grasp of the relevant economic concepts WRT view.ly may be lacking.

Could the squatter extort a fee from a large hypothetical user

No.

If the squatter is small, the brand owner can outbid them easily.

If the squatter is large, say Pepsi steals Coca-Cola brand, well, Coca-Cola can take them to court because they own the trademark.