In the end the answer to this is that some of the content servers are still putting things in the orangebox/bin folder that belong in the orangebox folder. There for the HLDS thinks it updated the right files, but since it's in the wrong place the EXE uses the old file that I put in the orange folder last time the content servers were loaded incorrectly. This in turn happens to be the old content 10 stuff. Anyone listening that works on the content servers please make sure that they have the correct file structure. This is also the cause to all the can't find whaterver.dll startup errors people are getting. Not sure exactly which files are wrong, but if you copy the entire orange/bin folder into the orange folder the exe will work.
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