I would not use KML in such case, but better JSON.
You can paint the vectors directly in OpenLayers - just merge your
viewer with functionality from:
http://www.openlayers.org/dev/examples/vector-formats.html.
This gives you on the right side of the page the JSON code for
individual features, which you can copy&paste and display later on as
a merged overlay layer.
Alternative workflow using HTML Image Map was described here:
http://groups.google.com/group/maptiler/browse_frm/thread/06ef448fc8a4ab46/14917e0653cf945f
There is plenty of tools which allows you to prepare image map,
including PhotoShop or Gimp.
You can specify the areas even online with a tool like:
http://www.maschek.hu/imagemap/imgmap
Once you have imagemap you convert it to JSON via script from:
http://goo.gl/GEg09
The JSON format displays fast in OpenLayers.
Here is an example code:
http://ligamen.org/work/test/openlayers.html
Visual part can be modified with OpenLayers.
Regards,
Klokan
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