Try downloading the latest Windows 2000 Compatibility patches, if you haven't already done so. I know that there have been a few releases of compatibility patches, and one of them fixed Half Life. Service pack 2 might be helpful also. (Of course, if it's not broke don't fix it)
the compatibility update solved all the problem with games in Win2K. I haven't had a problem with a single game so far in Win2K after the compatibility update.
What you need to do is download the update for half-life. Half-life was made way before windows 2000 and therefore half-life detects the os as an incompatible one.
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