Dont buy anything, the free/open source software is every bit as good as the comercial stuff.
Download Scid (or Scid vs PC) and a few engines, houdini 1.5 and stockfish 2 are good enough to kick GM butt, and all free.
Chess Software for Playing Set-Up Positions
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As a 1200 player I would like to purchase software where I can set myself up in a strong position(a piece advantage) and watch the computer still crush me. I think you can learn a lot when you can't win when you should. Any software suggestions?