I’ve noticed over the last couple months at least that Plexamp’s repeat feature doesn’t quite seem to be able to handle longer playlists. It can handle repeating an album just fine; however, when I create a playlist with a few dozen songs (about three albums, or five hours worth), only SOME of the tracks seem to repeat-- that is, when the end of the playlist is reached, rather than looping all the way back to the beginning, it loops to somewhere in the middle and plays from there.
With longer playlists/queues, repeat doesn’t work whatsoever. Sometimes, when a playlist/queue ends, I can catch a brief snippet of a song beginning to play; however, Plexamp always goes silent and kicks back to the home screen when a playlist/queue ends. I frequently like to hit the shuffle button on artists to just listen to their music on repeat, but this bug makes it tricky to do so, as I have to be able to manually restart the playlist at some point.