The small street where I live is positioned between two radically different neighborhoods on the Cambridge/Somerville line in the greater Boston area.
In one direction is an affluent Harvard neighborhood with brick sidewalks, historical mansions, romantic gardens, and overarching trees.
In the other direction is a stretch of concrete lined with multi-family houses with faded vinyl siding, shopping plazas, warehouses, and unfinished construction sites behind chain-link fences.
When we first moved here, it amazed me that two neighborhoods of such different character could border each other so crisply: There is no overlap, it is as if someone drew a line between them. Over time I got used to the divide and just accepted it as a given, but having begun cycling made me hyper-aware of it once again.
Cycling towards Harvard is relatively tranquil, with roads that are in reasonable shape and motorists who seem accustomed to bicycles. I would not go so far as to call it a "Disneyworld version" of a vehicular cycling experience, but close to it.
Cycling in the other direction, the roads are covered with pot-holes, the drivers are more aggressive and impatient, and traffic patterns are chaotic. Recently, Somerville has painted "sharrows" all over the major roads and this has helped a bit with the driver aggression. A bit.
When I first began cycling, I dealt with this by staying away from Somerville and only going to destinations that could be accessed via the calmer Cambridge route. But in the long run, this was not a reasonable solution. So I started to get myself used to the area by cycling with the Co-Habitant. Gradually, the anxiety of it began to subside. And then, one morning I got on my bike and rode on my own to a hardware store that is in the very thicket of the area that used to intimidate me. It suddenly felt fine.
I know that there are many, many people who cycle through Somerville constantly and probably find my comments here ridiculous / pathetic, but so be it - cycling there used to honestly give me anxiety attacks. No more though. In some ways it is up to the person to make the area where they live accessible to themselves.