On my first day I literally walk across the city, to the extent it can be done…The next day I do another cross town walk, but in a different direction, filling in the blanks from the prior day’s walk.
Then, over the next week(s), I walk between 10 to 20 miles per day, picking and choosing from what I have seen before, highlighting what I like, what I want to know more about, refining the path, till by the end of my trip, I have a daily route that is roughly the same.
While that is certainly not the most efficient way to see a city, it is the most pleasant, insightful, and human. I don’t think you can know a place unless you walk it, because it isn’t about distance, but about content.
I think part of the difficulty in allowing ourselves to properly delight in the imperfect, comes from conflating delighting in something with wanting it to happen. This isn’t the case. You can appreciate something as it exists while acknowledging its problems. You can see that a fire is beautiful without becoming a pyromaniac, and you can appreciate the absurdity of your political situation without thinking it’s good.
Even if a delight in the imperfect causes you to want more imperfection in your life (and it should), there is no shortage of imperfection to seek out. The imperfect is not scarce, it’s abundant. If you find imperfection delightful, you will never be short of things that delight you, even if you fix any given problem. Solving problems and smoothing out imperfections doesn’t remove the source of delight, it merely opens up new vistas for it. You could give yourself over totally to delight in the imperfect and never run out of things to explore, even without creating your own.