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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.
There’s a bit going unsaid in this Crouch End vs Catford conversation, which is that people will generally pay up to be far away from obvious signs of deprivation, and if you have £1m you probably want to live around other people that have £1m.