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1) As long as you simply log into Steam with the same login, you'll be able to redownload the games. There's a way to actually save the games by moving them to a USB drive or the like, but I'm unsure of the exact method on Mac.
2) Games which use the Steam Cloud will keep progress, games which do not save progress on the hard drive somewhere. It varies by the game, so I can't give you any advice here (I can only give advice on common PC locations).