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I'd use a shape layer and the Trim Paths path operation rather than a paint stroke.
There's a link to a video tutorial showing how to do this in the "Alter shapes with path operations" section of After Effects Help on the Web.
But, if you are using a paint stroke, then you can decrease the value of the Spacing property to make the strokes more smooth and continuous. See the "Brushes and the Brushes panel" section of After Effects Help on the Web.
[Edit: Oh, I just realized that just meant "smooth" as in having fewer and less sharp turns. For this, you should copy the Path property of the paint stroke, paste it into the Position property of a temporary dummy layer, run the Smoother on that motion path, copy the motion path, and then paste that into your paint path. If you just want to edit the path a little bit, then you can copy it into a mask path and use the mask path editing tools and techniques. David Wigforss has a tip about this on this page. The basic thing to take away from this is that you can copy and paste between the various kinds of paths and use the tools for one to help you with the other. (See "Create a mask or shape from a motion path".)]
Regarding the shadow: There are many ways to do this. The first that comes to my mind for the paint stroke is to duplicate the stroke, make it a dark grey, reduce its opacity, and offset its position slightly from the other stroke. (Each paint stroke has its own Transform properties, so you can just go into the duplicate stroke's Transform property group and add a little to its Position values.) If you decide to go with the shape layer option, you could do essentially the same thing or you could use a Drop Shadow layer style.
Many, many thanks for your quick and very helpful response. I was able to get both methods to work...as an added affect, since the two points were pretty far away from each other, I would zoom in on the starting point...zoom and pan out and then zoom back in on the destination. When I did that, the shape layer didn't work well because the method I used to "zoom" in on the map was to keyframe the scale property of the graphic I had imported from Photoshop and the shape layer didn't scale in the same proportions as the map...so I precomped it, but then when I scaled the precomp it pixellized very badly. I did get it to work by changing it to a 3D layer and use the camera function to zoom in and out. It was nice to have both options and thanks again for your very thorough and quick response.