Pimlico had already been made, rather than merely found
Let us suppose we are confronted with a desperate thing--say Pimlico.
The joke chooses a London district rather than an imaginary wasteland. Grosvenor's account of its own estate describes Pimlico as a nineteenth-century development by Thomas Cubitt: marshy ground was reclaimed and laid out as a grid of terraces, largely attracting the middle classes. It also records charitable housing projects there in the late nineteenth century. This is a modern institutional history, not a contemporary witness to what every Edwardian thought of the neighbourhood. Grosvenor, ‘Our history,’ section on Belgravia and Pimlico.
That background sharpens the experiment. Pimlico is already an instance of people turning land into a designed urban environment; Chesterton asks what could make its inhabitants undertake a further transformation. His extravagant comparison with Florence measures the imagined result against a city assumed to be beautiful. ‘Desperate’ and ‘awful’ belong to the comic provocation, not to a demonstrated survey of Pimlico's living conditions. The argument does not require the district to have been uniformly squalid: it requires a place the reader can imagine dismissing, approving complacently, or loving enough to change.
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