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The whole system + setting is stylistically based on oldschool pixel art games, so the map is similarly fashioned. The end result will show land, water, major settlements, and major highways.

Here's an example of the level of detail I'm aiming to have everywhere.

Click image for larger version. 

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And here's a video of how much I have finished/started, as well as the overall shape of things.

https://www.youtube.com/watch?v=ks75ZOYX2to

I'll be working on and iterating this one for quite a while I think, but I hope to host the end result on a website and add some navigation functions similar to google maps.