Hello,
I used to work for a vehicle tracking company and I have experience working with geocoding services (Google, OSM, Bing, regional providers).
I also have experience with GIS libraries (shapely, fiona, rtree), formats (SHP, KML,GPX) and applications (QGIS, Google Earth).
The distance to boundaries shouldn't be a problem once the addresses are geocoded; can you give me a bit more info on the addresses (what do they represent, what services have you used so far)?
Best wishes,
iticus