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yet people pay serious money to live there.
Right but Islington has two well connected tubes, a few over grounds and a million buses taking you to exactly all the places you are likely to go. Depending which side you're on you can walk to most of the City in 20-35mins.
I think Nickcj point was that Crouch End has lots of inconveniences, but being near the poor and homeless (like say Finsbury Park) is not one of them. I haven't spent enough time there, but it's the same feeling you get from people choosing East Dulwich over Brixton.
Islington has the greatest disparity between haves and have nots in the UK, yet people pay serious money to live there.