How does experience affect how you view a place?

To what degree do you think where you grew up within the Chicago area affects how you view the city? Two extreme extremes: Person A grows up in a posh north shore suburb, relatively close to the city, serviced by rapid transit, and is raised frequently taking advantage of Chicago's many cultural institutions as well as shopping at the finest of stores, and eating at the finest restaurants. Person B grows up in a poverty stricken neighborhood of the city, and is quite accustomed with the non-friendliness of the city. Gangs are part of the way of life where this person is raised. Would one person inevitably love Chicago more? Would it be the same? What are your experiences? Do you find that people who have had a relatively 'easy' Chicago experience love it more? Or is it the same? Is your admiration for Chicago tarnished at all by its 'dirty laundry'? Would you love Chicago more if it had even more cultural offerings?>