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Not sure what you mean - as long as both machines have the correct path set to the calibre library folder they will both find it. When you tell Calibre to use a particular path it looks to see if there is already a database there, and if there is simply uses it. The path settings are stored locally on each machine, so it is quite possible for them to be different.
What is more likely to happen is that you might get error messages about the database being locked as I am reasonably sure that calibre's locking strategy is likely to be the default and not take into account possible multiple-user issues.
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