I really wanted to find a vector way to do it so I could make one, semi-detailed map of the entire city and then just zoom in on specific parts of it, add a tad bit of detail, and have close up maps of different sectors of the city. This wouldn't be feasible with pen and paper (unless I had a HUGE piece of paper and a massive scanner) and raster programs can only zoom in so far. To get it high enough resolution to zoom in far enough may just threaten to kill my little laptop.

I do not want to do pen and paper. I am no professional artist and make too many mistakes to not have an undo shortcut.

If I can't find a way to make it look not completely perfect like a regular vector design I will just work hard at improving my accuracy with my tablet and 'draw' it in GIMP by tracing with a pen like brush. I still really want to have the flexibility and power of vectors, but if I need to I can give it up. I would rather have a more authentic look than have the flexibility.