B'more is hardly the ideal American city. Neither is D.C. Chicago is high crime, high taxes, high prices.....
So I'm not so sure that Jacksonville is all that bad compared to others (I'm a Floridian but admit I don't know that much about how it is to live in Jacksonville).
Khan, as with too many other NFL owners, seems more interested in talking politics the last few years than in making his team better. And, it has to begin with a financial commitment, and then next to finding the next generation of good HCs and GMs. But he seems to fall back into guys who have just emerged from the football Way Back Machine. Don't know if that's the best he can do because of a bad reputation; or if he might simply have no eye for football operations talent.