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+1 for the legend.
I'm about to start an overland sandbox campaign and having some differentiation in the tags will be very important to make the map easier to read.
I would also like to second the idea of having a small image be a possibility in the mouse-over information. That, combined with colors to differentiate pins, would make my day. That way a pin colored as a "settlement" could have a different icon if it was a village, a town, a city, or even a trading post.
As long as you have an easily accessible Legend, I don't think confusion will be much of an issue. Also, if you tied the Legend entries to the topic types, (like "settlement" or "adventure area") I would think it would be possible to have the colors automatically assigned when you connected a pin to an existing topic. Of course, that's my non-coder, design minded self talking - I obviously have no idea about the technical hurdles involved in any of this.
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