A street observation exercise becomes more manageable when it follows one visual theme. Choose colour, repeated shapes or the relationship between doors and windows. A familiar route can provide enough material without requiring an unusual destination.
Walk at an ordinary pace and make brief notes from suitable public viewpoints. Notice patterns before deciding which deserve a photograph. Keeping the theme narrow helps separate a thoughtful sequence from a collection of unrelated attractive details.
Review the observations together after the walk. Look for similarities and exceptions, and describe them without inventing stories about the people behind the buildings. An architectural detail can be interesting on its own terms.
Arrange a small selection with clear captions about what you observed. A personal visual essay does not need to claim that it represents an entire city. Its strength can lie in a precise account of one route and the particular question you brought to it.