If your question is something like 'where can I expect puddling and flooding you will not achieve this with a flow accumulation surface. Flow accumulation is returning a new grid where each value is the number of cells that flow into that cell. Your urban area has a vast network of storm water facilities that are not accounted for meaning your flow ...
Solution using cost allocation tool from Spatial Analyst. Populate short integer field in polygons by 1. Convert polygons to raster, using this field. Expand raster by 1 cell, output is your cost raster in cost allocation (CA) tool.
Use it and road centrelines as source in CA.
Output cost allocation raster:
You can convert allocation raster to ...
This is a large radius, so this will be computationnally expensive. That being said, focal stat is the good tools if you have only 1 and 2 values: make the sum of the cells with focal stat, then
"percentage of cells == 1" is equal to 100*(2*(number of cells in the radius)-(focal stat result))/(number of cells in the radius)
I created a simple model in ArcMap ModelBuilder that adds the shapefile name as a new field in the shapefile. I assumed that your shapefiles are all in the same folder (Test) and not in sub-folders. If they are also in sub-folders, make sure to set "recursive" in the iterator tool.
For the add field tool: make sure the field type is set to TEXT, ...