The most helpful question for Colton to ask himself when trying to date and learn more about the photograph would be:
What is visible in the photograph? How are the subjects arranged? Are there any textual clues or signs visible?
This question encourages a detailed analysis of the content of the photograph, which can provide valuable context and clues about its time period, the people or events depicted, and potential historical significance. Understanding the arrangement of subjects and any textual elements present can lead to insights about the photograph's date and context.