[Q] Random music sync with memory option??

Im looking for a desktop media library/music player that allows a random song sync with android. I also want to limit the amount of memory it fills. For instance i want to set it to sync random songs out of my library to fill a max of 3gb.

Ive tried winamp but for some reason it only wants to sync full albums rather than individual songs, despite making sure the option is unticked under autofill options.

Im sure there must be something out there that can do this, seems like a fairly basic requirement to me!! Anyone found anything that can do this?

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