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What happens when I download Astro Gold to my iPad first choosing iCloud Drive and then to my iPhone next? Am I given an option or is it the first device that I choose iCloud Drive on that works?

You don’t get any option. The first device that you use to switch on iCloud determines what files appear in iCloud drive. When you switch on later devices, you lose access to your local files on that device, and instead see what chart files were already in iCloud Drive.