One of the barriers (I'll address that first) is that sometimes the citizens of a smaller town believe that having big named chain stores, a bland downtown, etc. are just what they need to modernize their towns. That is what happened in my home town a few years after I left: I still remember my mother excitedly telling me, "We're going to get a [insert big name chain store here]!" Homogeneity seems to be the new "modern". So that is one barrier as is the economic payoff for the city: when people visit, many will choose to buy from a business they recognize rather than taking a chance with an establishment they have not seen before.
So, I think that a shift in values has to occur: valuing the traditions and culture that were the foundations of the city previously. There is a reticence to do that because of the desire to be modern; however, if the citizens (including the elected officials) are offered the chance to value tradition while modernizing (mixed-use communities, e.g.), I think that most would go for it. How does a change in values take place? One small community at a time, and it must be demonstrated that heterogeneity is profitable :-)
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