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I’ve been riding in the city for 8 years. All sorts of bikes. For 2 years my job was to ride bikes and promote cycling for CDOT. I’ve been to every nook and cranny and rode my bike to get there, all the while locking it up in the ‘worst’ parts of the city and for an entire year I locked my bike out front my loop office near city hall.
I use a small ulock around the back tire through the triangle. I would sometimes use a cable lock. I have (knock on wood) only had some straps stolen in Rogers park 5 years ago.
Basically though I would bring my bike inside any opportunity. I’m not worried about most people in neighborhoods stealing my bikes. But I live on the west side a block away from the 606, the Puerto Rican fixie goons around here will steal your shit.
But black neighborhoods are fine, they don’t drool over bikes like Mexicans and PRs do, plus they don’t have the tools to take shit apart.
My geared bikes have locking skewers and anything that has a Brooks I have cable locked.
I asked /n/ 10 years ago these same questions before moving here and I’ve kept the same mindset; if they want your bike they will take it no matter what. The point should be to make it more difficult than the bike next to you. Oh and don’t have something to flex with, it’s just asking to get stolen.