Some ideas:
ESRI Local Government Information Model Public Notification Tool. I have not used this, but it may be worth looking into.
http://solutions.arcgis.com/local-government/help/public-notification/
If the goal is indeed to traverse 500 feet out only accumulating distance across parcels (ie the distance across ROW does not count), I'll throw out some preliminary workflow ideas (untested) on how it may be possible to solve that. Note that these will need to be fleshed out a bit and they would be an interesting challenge for someone to implement (i.e. not a simple solution quickly done):
- If one has access to the Spatial Analyst Extension, create a Cost Allocation or Euclidean Distance. Make ROW zero and parcels a value of 1. Once the distance surface equivalent to 500feet is found, convert from raster back to vector and do the parcel selections. http://desktop.arcgis.com/en/arcmap/10.3/tools/spatial-analyst-toolbox/understanding-euclidean-dista...
- Use Near or Generate Near Table, then construct a line based on the angle and distance, then Erase from the line the ROW polygons, then sum the line segments total distance and see if it is 500 feet or less. A Python process to do all this automatically for all the polygons in an area around a selected polygon would be optimal.
http://pro.arcgis.com/en/pro-app/tool-reference/analysis/near.htm
http://pro.arcgis.com/en/pro-app/tool-reference/analysis/generate-near-table.htm
http://pro.arcgis.com/en/pro-app/tool-reference/analysis/erase.htm
Chris Donohue, GISP