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It depends on what you want to do with the files. To play them remotely via the server, the server would have to connect to your remote player. Then it could access your local files and stream them to the player. I guess you would need a direct VPN tunnel between the two devices for this. To control the server you would need of course a remote connection to the NAS too. Where you store your files is relatively unimportant, as long as the server can access them. However, it probably makes the most sense to store them on the NAS so that you can always access them.