Have you looked at this book called "Stroll: Psychogeographic Walking Tours of Toronto" by Shawn Micallef? I've had it for a few years but haven't really done any of the walks (as noted above, I like to just go and wander, taking different streets I've never been down, etc.). However, I was recently reading it and think I'd like to bring it along for a walk. Tonnes of interesting information about the various walks.
actually a lot of map making is about subjectivity and understanding the psychogeography of a landscape in ways that a computer can't. So while computers have aided in map making in a big way there is a large place for humans in mapmmaking.
For example, maps of neighbourhoods, ethnic enclaves, green spaces, culinary maps, soundscape mapping, art gallery walks, historic landmark maps,
My favourite book on an example of subtle psychogeographic details in maps is called Stroll.
http://www.amazon.ca/Stroll-Psychogeographic-Walking-Tours-Toronto/dp/1552452263
there was also a great podcast on monocle recently about hidden layers of cities uncovered by human made maps recently