This is such a huge need for real estate and insurance professionals, to be able to grab a map and pin content onto the map. You might even want to upload an image or map and then mark out areas that display a pop-up when you hover over the image.
The software that I’d recommend you check out is Pictogon for map & image annotations that you’re going to want to display publicly. If it’s for internal use, you could use design proofing tools to mark up the images but they don’t have the same feature of being able to trace the outlines of objects and then add labels.
You could also look into using Canva if you’re after something that can annotation the image without having the visual pop-up feature.