For people that value cultural diversity and unusual opportunities, cities like Portland and San Francisco are much better for that in terms of diversity of culture than most of the places listed (Austin excepted). I think trading space and amenities to live in a cooler, more interesting place is totally reasonable. If you are happy with a bike/public transit, and don't mind living in 200 sqft of space, and being around a thriving local art and music scene is important to you, why not.

Remember that what you value is not what other people value. Living in Tampa or Akron might fulfill your needs, for others it might make them question their reason for existence.