We're not even allowed to run cable between two adjacent properties owned by the same company. (A former employer of mine got around this with a "temporary" 3-phase cable going between the two, but it was regarded as a bit dubious.)

In many places the streets form a grid, it's true. You would possibly have only a dozen homes that could be connected. In other places, the streets are arranged as a tree with cul-de-sacs as the leaves. An island of acreage could emerge in such developments where you could visit dozens of homes without crossing a street.