I have met grown men - secure, strong, worldly men who are absolutely terrified of cities, particularly New York City. To city lovers like myself, these fears seem completely irrational. I understand the fear perhaps of an older person or single woman walking in a dangerous neighborhood at night - this is courting trouble. But a grown person in a vehicle in broad daylight with an entire family in tow? What can really happen? If you get lost, you will eventually get unlost. In my experience, the worst that will happen is that you will be very inconvenienced for some time.
The worst scenario to me is breaking down in an automobile in the city. Fixing a flat or getting a battery boost, simple acts elsewhere, can be a real headache here. Services are not readily available and waiting for roadside service on a busy highway in a traffic congested city is certainly not pleasant. And if one would have to overnight in a hotel, that would be mighty expensive or very inconvenient.
There is no plethora of basic services like tire repair - places like that in the photo are generally found in poorer neighborhoods and in out of the way locations. Unless you know a neighborhood well, these places are destinations - the likelihood of finding them when you need them is rather remote. And escalating rents have conspired to make these places all but non-existent. The scarcity has made this type of subject a popular photo.
Certainly being lost in a city or having trouble here, like getting a flat tire, is more troublesome than the same problem in the suburbs and there is perhaps some risk of exploitation by opportunists (although our suburban or country brethren are not immune from this). In most cases, however, a little cash or credit card will be all that is necessary to extricate oneself from virtually any situation. I remember a conversation with a client of mine when I was younger and very inexperienced in travel. She was much older, nearing retirement and planned to settle somewhere on the coast of Italy. At the time, this seemed such a fantasy and unfathomable to me for a number of reasons, language being one of them. When I asked whether she was concerned about not being able to speak Italian, she replied, she was not at all worried, because "they all speak American Express" :)