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paint challenged

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i scanned thru all the tutorials and lots of questions but still can't figure to paint or color an area with a transparent color. i have a street map image, i've saved, .jpg, and i want to transparently shade different areas of the map, so that the streets, names etc still show thru. something like school district A is shaded in light green, school district B is shaded in light blue, etc. so the paintbrush with a width of about 12 allows the control to follow the edges of the areas involved.

should be easy, right??



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