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It would be best to get up to the highest area you want to survey and launch from there. In this case you can set the overlap pretty low (60%) and the areas below there will get plenty of overlap and turn out nicely.
As long as you don't need super high resolution on the lower areas flying high is your best bet.
We do offer a feature that would allow you to show each of 5 different jobs as a layer in the same map (we call it a Location Map) but that is less than ideal in this case.
We are working to add terrain awareness to our planning and it will be available soon.