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The issue is not related to Windchill itself - you're getting errors when installing Oracle.
There should be no problems installing Oracle 10g on VMWare - many people use it on production and test systems.
What guest OS are you using? Make sure the Oracle 10g is supported on this OS. Aren't you trying to install Oracle 10g on Windows Server 2008 R2? Also, are you on x32 or x64?