interesting. take away the handdrawn feel, and i see this as a perfect example of the possibilities of a geo-tagged location search. imagine popping open your gps-enabled laptop or cellphone in a specific location, and adding a little "tag" or note to an online database, a la google maps. later on, go to "tourist" mode or "wiki" mode or whatever, and all over the map you see people's little notes displayed. i think if you looked up wiki maps on a search engine, you'd find basically the beginnings of services like this.
This is the sort of map/art/community project artists have been doing lately. A combination of psychogeography and community participatory mapping.