I had an iPhone app on my iPhone 5s now currently under repair that had a $100 app called GIS kit.
I am connected to my iTunes account with the App Store, and have a bunch of apps that it's allowing me to download via the cloud download icon, but not this one.
So, a really quick way to answer this question would be with another question, and that is, does Apple even allow app creators to charge users twice for what is supposed to be a one time payment for an application?
I just activated this phone, have not done a hard reset or anything like that, so I'm hoping the GIS kit application simply just does not recognize that I have already downloaded it. But it could be something else, worst-case scenario I actually have to pay for it twice. Hope not.