Originally Posted by skip252
If the E365 is like other Sonys the limit you can make on the player is 5. You should be able to make as many as you like when you connect to your PC as long as it's Windows with Windows Media Player 10 or better installed. That allows to be transferred to the player as a MTP player instead of a drive letter.
After the files are transferred you can right click them in Explorer to bring up the context menu that includes "create playlist". Name the playlist and once it saves you should see the playlist and included songs after you disconnect.
Any MTP enabled media library will also let you sync files and playlists from your PC. MediaMonkey, Winamp and MusicBee are a some of those. Winamp and MusicBee will even let you use the files on the player to create playlists without syncing.
I haven't noticed Sony make many changes in the E series players in the last few years. Any threads you find on them and probably the A and S series player will quite possibly have information that will apply to the E365.
Lots of information. Thank you.