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I am a new user and I want to play Skyrim.  I am trying to use a version from the Steam store.  Do I need to buy it before I start to install the program on Play on Mac or will I be prompted to do so at some point?  The broad version of this question is how exactly do I get Play on Mac to read that I own the program I am trying to play?

You need to install it, and when prompted, it will ask you to log in, and when you log in, it should take care of installing it for you. Steam has ID numbers to refer to the games, so after the virtual drive has Steam installed, as well as all of the other stuff it needs to run it thorugh PlayOnMac. After it is done with the install, launch it from POM, and it should prompt the Steam login and stuff, just like Steam would normally. The script simply prepares the virtual drive so that particular game, when installed through Steam in the drive, will work as it should.