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If you purchased the StockSpy for Mac Pro in-app-purchase you don't need to pay again to activate Pro on a new or second Mac...
Make sure you're logged into the Mac App Store with the same account you used before. Use a pro-only feature to begin the purchase process. Repeat the purchase steps to register pro. After that you should see a message saying the purchase is free since you already own it. If you have any problems please contact stockspy@gmail.com