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If you look at the console in any Source game (HL2, Portal, etc.) you'll always see errors of one sort or another about missing files and the like.
As far as real errors go, the only thing I seem to recall having problems with, aside from random crashes, was to do with Python. It wouldn't run with a newer version I had installed. But that was years ago - I think that was addressed in one of the unofficial patches.
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