Robert,
Please note that I'm a software developer, and I have almost now idea about GIS, despite the fact that I really really like this area of study. I'll read few books about it, but I don't have that much time now.
This is what I have done:
I remove almost any feature in the map, and only keep highways. It means I have an osm XML file that contains only information about highways in the city.
This is what I want to do in plain English (not gis or software ...)
Alongside each highway I consider a width of 30 meters for example. Know I have a very long area with the width of 30 meters in one side of the highway, and same on the other side of they highway. They are separate areas.
Now, I need to divide each big area to small areas, for example each 50 meters long, so end up having a lot of 30*50 meter areas. I don't need them to be exactly equal, almost equal suffices.
Now I need to add some points, etc. to each divided area, and may need to monitor them and give overall maps about them, which geotrellis is great at doing that.
Now what can I do? Please give me step by step advise, since I'm a little unfamiliar in this area. If you think some documents, books, or resources will help me, please name them.