When I specify the same path multiple times, it seems to just use the configuration for the first time it was specified. This is undocumented however and I'm not sure if this behavior is consistent and can be relied upon.
This behavior can be useful, for example by specifying one extra field for logs/specific.log and another field for logs/*.log. This would specifcy specific.log two times. This second time just gets igored it seems.
It would be nice to know if this behavior can be relied upon (and if so, I think it should be documented in the specification of the files field), and what the details of this behavior would be.