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Apple Maps might be a bit more popular than Paintmaps.com. We know about 1 link to it since March 2021 and only 1 link to Paintmaps.com. We are tracking product recommendations and mentions on various public social media platforms and blogs. They can help you identify which product is more popular and what people think of it.
You can also import images to edit. So for example, you can import a blank world/region/country map and then manually put borders and colors with GIMP. Alternatively, if you're unsure of your skills with GIMP, you can use https://paintmaps.com/ to paint regions, countries etc., and then import the image to GIMP and make whatever modifications you want there. Source: about 3 years ago
Regarding bullet 6, I thought Apple Maps doesn't collect travel history? I looked on apple.com/maps and this is what they say:. Source: over 1 year ago
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