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Thank you for your questions and for your work as a Citizen Archivist. I think the answer to your question is both. Typically we suggest tagging the features on a map. If the map has a title or paragraph explaining the contents, mapamaker, etc. that should be transcribed.
As for the photo question, if you can read a sign and it feels significant, go ahead and transcribe it. Please include in brackets some description such as [handwritten text on protest sign] along with the actual transcription.
Community Manager, National Archives Catalog