Great job everybody! I had a lot of fun with those challenges.

For the “Ways Need Smoothing” challenge, another possible reason for false positives that I noticed were Interstate crossovers, splits, and merges. They would look super sharp as you cut over from the northbound lanes to the southbound lanes, for instance. I ran into a few of these. Some I smoothed out, and others I skipped because I wasn’t sure.

Sounds a little like Chicagoland suburbs. Areas not incorporated by a city would receive an address prefix based on a mile-wide grid centered on Chicago. So, a north-south street a little more than 3 miles north of the centerline would be 3N###.

The problem is, the numbering system is zero-based. I have an address that is 0N###. This doesn’t work well with most address searches. I often have to drop the “0” when I want directions from most major direction search engines.

To handle the middle of the road issue, you could evaluate the similarity over an arc or a line across the road. Instead of picking the first point that’s similar, gather a list of points along the arc that are similar, and pick the one in the middle. A little slower, but it might work.