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Topics - AirHead

I'm new to this and not sure where to begin.  I need to create a custom map or overlay (or something else?) that has these three features:

- Identify polygon areas on the map and shade these areas with specific colors (red or yellow).  These areas are generally city lot size, but could be industrial plants, city parks and so on (some larger than 400m in one or more direction, some not even that big).  Proximity alarms from the borders of these would be very useful.

- Custom points of interest (symbol).  Proximity alarms would be useful on some, useless on others.

- Display arbitrary boundaries: 5 nautical miles from the stadium, 2 statute miles from the penitentiary, the key hole shape that surrounds an airport on an aeronautical chart and so on.

It would be extremely useful to associate a name (32 characters or less) with these.  It would also be useful to associate text with these (even if it is just a comment in an XML file).  Specific colors have meaning for these features.

I have no idea where to begin.   I don't know of a POI file has this capability.  Do I need to modify an existing map?  Or something else.  Any advice will be appreciated!