Having lived in Boston, I can say that the city is way overpriced. You may argue that rent is in line with what people are willing to pay for it and that may be true. However, the city is failing its residents who have no protection against unreasonable increases (due to a state law) and new development is nowhere near strong enough. At least in cities like SF, Honolulu, and NYC you trade affordability for hire wages, natural beauty, and nightlife. Boston is nothing special in comparison.