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The Masquerade module currently does allow for testing site functionality for guest users by entering "Anonymous" in the masquerade block as the user to masquerade as, but it does not allow for creating "Quick Switch" links, as the module admin form complains "Anonymous does not exist. Please enter a valid username." on any attempt to do so.
Another related quirk is that masquerading as "Anonymous" is case sensitive ("anonymous" is not recognized as valid), but masquerading as an existing account is not (entering the name "tEsT uSeR" will successfully masquerade as user "Test User").