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I have a map of Canada. I am going to create regional boundaries within the map that go beyond the existing provincial borders (for example, this map illustrates the four regions I will use to divide the province of Ontario) and then highlight those regions with different colours.

I will need to repeat the process of highlighting the regions I have created with different colours multiple times to create about 30 different maps. All maps will have the same defined regions but each map will be coloured differently.

What is the best way to approach this task in Photoshop?

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Once you select an area you can use Select > Save Selection to reload that selection later via Select > Load Selection.

An easier method may be to create individual layers for each area. Then you can merely apply a Color Overlay layer style to change the color of that specific area. And then subsequently change the overlay color to change the color. This takes a bit more time to set things up as separate layers, but if you have to create the selections anyway it would be worthwhile in my opinion.

Ideally you'd do this with Adobe Illustrator so that each area is an object, then recoloring an object is just 2 clicks. But without understanding the complete workflow and desired output, it's hard to say if that feasible for your particular situation.

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    +1 for recommending Illustrator. And even better than making each area a separate object would be to do all the map's edges and borders as paths, and then use the Live Paint tool. – Wildcard Jun 23 '17 at 0:36

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