If you're worried about sightlines in a 3-D world (which is what it is), then I'd consider visualizing the world as a huge 3-D cube. Each point on the cube has different properties, and would thus be a node in this 3-D grid. One of these properties would be opacity - does light pass through? It then becomes very simple to write a procedure (if it hasn't already been done) to determine the points the sight vector would pass through, and determine where it stops. Weather would also be implemented as a modification of these values. You can get wind (for people flying on griffons), etc.

This also allows for a very easy way to handle underground activities, and how those activities would interact with the rest of the world.

Now, you would have a world grid, then a grid within each of the major locales, like Waterdeep or Undermountain. This would be a sub-grid, sorta. At (40,23,0), there is another grid for that place. You enter the sub-grid at a defined point, depending on where you came from.

Another point that has to be made is that D&D is owned by Wizards of the Coast. I know for a fact that they tend to frown very heavily on people writing stuff for public consumption based on their intellectual property, even if you're distributing it as free-ware. So, if you wanted to do something serious, you would have to make it for private distribution only. Sorry, but you don't want their legal department hitting you with a cease-and-desist. (For examples of this, check out www.mtgnews.com and look in the news archives.)

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