Earlier, I was examining this horrible and horrifying stretch of road while waiting for the bus, with ramshackle houses not too far away. It struck me as crazy that in a city as good as Portland, that there were still such bad spots. And then I decided it meant that the United States is still a developing country, not much better than the 3rd world
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Add semi-trailers, forget it.
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There are now robot repavers that lay cobbles like a bowling alley pin setter, or perhaps like a modern mechanical Gandy Dancer.
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If the city finds a reason that the street *must* be paved, then they can make you pay for the upgrade. Otherwise, if you don't want to pay, it won't get done.
Keep in mind that paving the street will also raise property values,thus increasing the property tax owed by folks along the street as well.
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As I said, unless there's a *very* pressing need, the city isn't going to exert eminent domain and force the people to pay for the paving (initial paving is a lot more expensive than minor repairs later).
So as long as the majority of the folks along that block aren't willing to pay for (it's only partial payment as I understand it, but it's still expensive) the street will remain unpaved.
The city is responsible for *maintaining* the streets. *Improving* them (at least residential streets) is up to the property owners.
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