Quote Originally Posted by Iggy View Post
I can easily transform a flat land map into a globe in Winkel Tripel but I don't see how that brings me any closer in making a proper globe map.
I think you've got this a bit backwards. The "real" shape is a globe, as in a 3D, close to spherical shape. Any map is a distortion of the globe because it's flat, while the globe is not. The particular way that flattening is done is the projection.

You can think of it as if you put a light at the centre of a clear sphere with the features painted on the surface. Then held a flat piece of paper up to the globe, and traced out the shadows cast on it. This particular projection is called Gnomonic and it's used in geology, and for building projections on the surfaces of polyhedra. Other projections role the paper into cones or tubes, move the light, or even bend the light or do other strange things.

So don't think about drawing a flat map and then putting it in a projection. Think about drawing in a projection, and then changing to another projection. You need to draw the distortion for the first projection into the map otherwise when you change projections, you'll get the reverse of that distortion combined with the distortion of the second projection. Even if you stick with the original projection, you still need to get that distortion right or the map will look wonky to anyone familiar with real maps.

One thing to ask yourself is, just how much area does the map need to cover? Do you really need a map of the whole globe? Smaller extents are easier. You still need to think about where you are on the globe and pay some attention to projections, but it's a lot easier. You should also think about what kind of map it is and what level of cartographic and surveying sophistication was employed. It might be that dropping things you are used to seeing on modern maps like graticules, compas roses, scale bars, or even trying represent the spatial relationships between things at all will make your life easier. In the times most fantasy draws on, maps were fairly rare, and tended to be more topologocal than topographic; they were about connectedness rather than shape and distance, more like a modern subway map. They also had very poor source material to work with.