Load your files on playlist:view/manage/simple add and after that go setting/ preferences/playlist/ckeckmark on play files randomly forever/save.If you checkmard advanced options you have more choices.
I am using VLC media player 2.0.3 Twoflower.
I could PLAY all files from playlist.
1. Goto tools -> preferences -> [CTRL+P]
2. At the left bottom corner, under Show settiongs select 'ALL'
3. Check all 3 botttom options i,e i) Auto start, ii) use media library, iii)Display playlist tree.
This is working for me. Hope it works for you too.