When to Repair?

How do we know when something needs to be fixed or it's just character? There's this one street I walk on and the sidewalks dip down or up, there's cracks running through them, and they're covered in spray paint. Along the way the houses paint is peeling, the stucco if chipping in strips from the steps, but there are flowers outside. I think it adds to the charm, yet it's certainly run-down and in need of repair. So when do you make that change?