
In Japan, maps in public places such as train station and street, are oriented to the direction you are physically facing it, instead of always pointing North at the upper edge of the map.
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Map in Train Station
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North Is Pointing Downward
Some problems:
Map Production – this convention means that every map in public area has to be customized by install location and orientation. Mass production of the same map layout becomes difficult. Furthermore, if some local business information or landmark in the area is outdated, it costs extra overhead to update all maps in that area.
Online map printout versus street map – more people are using online maps service and printing out location info sheet before going to a destination. These maps, however, are usually generated with North always pointing to Up. As a result, you can often see people standing in front of a station map (North is pointing at random direction), with their map printout in hands (North is always pointing up), and turning the paper left and right attempting to align the printout with the station map.
Why? – as taught in Japanese school, the first step of using a map is to first orient the North to the right direction. It is considered basic knowledge. In contrary, western map system is always assuming North is Up. This difference has to be taken into account when making navigation software.
However, when designing Google Maps, it seems that the engineers are likely to follow the western system, so they would just pre-generate map tiles that are all orienting north to upper edge and serve static images to users.
What makes it more confusing is that, now that more people are using handheld devices with digital compass built-in to read Google Maps, engineers take advantage of the technology and rotate the tile with the compass direction. Result: the map tile rotates, but the labels are not re-oriented to upright readable position.

Google Maps on iPhone, can you read upside down?
Some suggestions for map software, web-based or mobile:
Rotate labels on map – generate map tiles on the fly with labels properly oriented to user.
Adaptive road display – Display more details info like landmark, convenient store, and small alleys near the centre of the map, and rougher data and roads when it’s further from the centre.
Allow manual map orientation – don’t just rely on digital compass, but allow user to manually rotate the map with two finger rotation gesture. Digital compass works really bad in city full of buildings and interference.
Japan specific: Cho-me (block number) – visually group a block with colour-code, shade, outline etc to make it clear where are the edges of blocks.