This is stuff you grit your teeth and put up with because it can't be helped. Who would choose to design a city with this decay literally built into it? That's mind boggling.
Leave cracks and potholes on the pavement for long enough, allow some dilapidated building to stand for long enough, and it just becomes part of the identity of the city and the people who live in it? It turns into the city's "character" ?
To me that sounds like a coping mechanism.
Like the roads actually being used and not closed so they can be constantly repaved.
Decay is a never-ending process, as are the changing architectural tastes of city residents. Only through a continual process of demolition and rebuilding can they be kept at bay.
You see this in real cities everywhere: districts of shiny, antiseptic, newly-built towers, side-by-side with decaying warehouses and brownstones from a hundred years ago. The former are modern, the latter are charming, to be desirable a city needs a balance of the new and the old.
The extreme opposite of that would hordes of people (or robots) with nail clippers patrolling everything 24/7. When any tile is even just chipped (or when when the scan shows the wind carried away a few molucules from the surface), it gets replaced. When tiles in that exact same color aren't available anymore, they all get replaced. Heck, when the sun was out and faded the color of something slightly more than areas that were in shade, the whole area has to be rebuilt.
Or take cutting your fingernails: do it once a week, do it daily, or why not every second? Every moment they're growing a bit, and they don't remain in the shape determined as well cut by their owner for even an hour! Unless you keep cutting/filing them. But while you are cutting your nails, you can't be cutting your hair, so that's gross. And even if you could, you cannot cut all strands of hair at the same time, it'll always be screwed up.
So of course the answer is somewhere in between, it has to be, and it's probably not the same for everybody.
Hordes of robots constantly and meticulously maintaining entire cities sounds awesome, actually. That's the post scarcity society I dream of.
> Or take cutting your fingernails: do it once a week, do it daily, or why not every second?
We only need to choose because we lack the technology. Maybe one day we'll have Deus Ex style nanobot pills we can swallow. They will invisibly and continuously maintain our bodies for us. Nails are just one of countless things they will maintain.