I think that could be cool, if it was done properly. If it was done wrong it could be too busy and/or too gaudy.
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I think that is a VERY cool idea -- the only thing I would be concerned with is people getting confused which squares are black and which are white. However, two ways to overcome this (right off of the top of my head): either have a tiny corner of each square colored black or white (like a little triangle of black or white in the same corner in each square) or maybe do some sort of layering of the board, where you can still see the black and white squares faintly, but the map overlay itself is more visible -- something like that. Either way, cool idea!
I just had this discussion with a good friend from chess.com.
I have an idea I wish to share with you, I believe I can trust you with an idea I have. I recently saw a chess set of NFL teams and the board looked like a grass football field, well that got me to thinking. You know how some people will collect custom pieces, The American Civil War, and Revolutionary War just to name two for now. I see these pieces in the local Malls and they are always setting on the same boring black and white squares. My idea is to have them set on a custom map or better put a battle map. Like "Bunker Hill" for the Rev. War or Gettysburg for the Civil War. I think the battle maps would be a great addition to the pieces themselves.
What do you think?