Divide into testing market/user-experience vs technical hypotheses: "Would it be fun" you can test by faking it, like curating it by hand for a small specific

Divide into testing market/user-experience vs technical hypotheses: "Would it be fun" you can test by faking it, like curating it by hand for a small specific area (e.g. a popular street in a popular part of a popular city; or your hometown; or somewhere that appeals/you want to visit). "Can I make a general algorithm using publically available data to do this for everyone, for everywhere, automatically" is the technical hypothesis. It seems like a really challenging problem! But because it is clearly defined and scope-limited, I feel it's more straightforward than the first one.