In a way yes it transfers the files. However, filepaths and filenames are not retained. Even after trying to configure them in the handheld options. Syncing throws them into a deeper path like C:\Temp\MyBasePath\C_\Users\rjt\AppData\Roaming\J River\Media Center 14\Temp. Additionally it appends some random four digit number to the filename like this - Keep It Going - 5160.mp3. Because it treats it as a handheld then it creates a .m3u playlist and .mpl database, which would not matter as long as the names and paths are duplicated after the sync.
My intent is to retain existing paths and filenames. I am looking into mapping a drive letter through a VPN. But this is not an area I have experience with and have not successfully done a mapping yet. Not sure if this the road to travel but a vpn sound helpful in a lot of other ways when I am out of my house and want to connect.