The neighborhood I live in is between 20 and 30 years old, other parts of Oakville are under constant growth. When a new sub-division is built the developer will put in sewers, roads and start building houses. Sometimes the street signs will look home-made other times proper street signs will already be up.
When I see a new subdivision going up near my I try drive (or walk) the roads with my GPS capturing the data for OpenStreetMap. Often my GPS traces in OpenStreetMap will be the first time these roads show up on a map outside of the towns GIS. It might take years before some of the commercial maps send trucks to map these roads.
On Sunday I was driving past a sub-division that was being built and decided to map some of the roads. I got about GPS traces and names for about half of the roads. I need to make a point of going back and finishing the soon. Sub-division construction sites usually have construction workers and heavy equipment moving about. It is important to pay close attention to your surroundings and the condition of the road your mapping often it is a work in progress.
I doubt anyone is going to be moving into these houses until the spring. In the spring when people move into their new houses they will be able to use OpenStreetMap to invite there friends to the house-warming party.