In my music app I created an array of media players (my case 2) and keep track which one is actively playing
When the active one gets within 7 seconds (user defined amount) I start the second media player playing (which was loaded when the 1st one started)
And then keep bouncing from one to another
Both media players playing at the same time seems to work fine?
Most songs have some type of fade out at the end and you can hear the 2nd player playing as the first is ending.