Option 1: Write a chapter per decade, listing who lived where, potted biogs where needed, and linking together to show how building use changed, and how the ‘cast’ interacted. And what the context was with World events.
Option 2: Write a chapter per house in the Square, showing how some occupants linked to the prior resident, the changing uses of each building, starting with a list of all the occupants. Larger biography for the most important person who lived in each one.
Option 3: Separate chapters by occupation or major themes ( railways, shipping, religion, politics, Civil War, writing etc ), grouping together similar subjects. Show the impact the Square had on these areas.
Option4: Don’t have an over-arching structure, but have one house through the whole century, one chapter on the Civil War, an example decade showing changes in popularity through the years, one chapter on ‘most notable worthies’.
Not sure which way to go at the minute. Again, feel free to suggest.