I can't answer questions 2 or 3 but I can give ya some pointers in Photoshop. Your coastlines look fine, by the way. First, scan your drawing . Duplicate the drawing layer. Image - adjustments - Brightness/Contrast = set the contrast to max. Image - Adjustments = Desaturate (this removes any stray colors). Now zoom in and make sure that all of the lines connect, we don't want any gaps...this could take a while. Grab the Magic Wand tool and click once in the ocean to make a selection of it. Select - Inverse. Make a new layer and grab the Paint Can/Flood fill tool and click once to fill the new layer with white. Select - Deselect. You now have your continents on their own layer. If the whole layer fills with white then you have gaps somewhere. If you want a more jagged coastline then there are lots of tuts to follow but here's what I do: New layer filled with black; move it under the continents layer; merge the continents layer down; Filter - Pixellate - Crystallize = 12; repeat but with 9 then 6 then 3; Image - Adjustments - Brightness/Contrast = contrast to max; Select - Color Range = black, hit the delete key then deselect. Now you have jaggy coasts on their own layer.