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I'm also a Mac user but my friend has the same problem on Windows 8.1
I'd repeat this process for Ep.1 and Ep.2 just to be sure, but for me it was just the one file in the main game.
I'm a fairly experienced Steam user and the scary thing about this is validation hasn't worked for me on any of them.
The console:
Unsupported 32-bit executable: "/Users/username/Library/Application Support/Steam/steamapps/common/Half-Life 2/hl2_osx"
So I've checked the web... it seems that somehow current version on Steam is 32bit, even though they've released 64bit version in 2007. Doesn't make any sense. I've tried reinstalling the game -- didn't work