I am sorry, this is not related with outlining.

One software I always missed from the Windows is the Mediamonkey.

I couldn't get anything close to it in the mac.


What I am looking for is an mp3 (audiobook) player for mac that could load the rest of the files when I click the first file.

Vox can do it: but, it has some annoying privacy issues: it has some virus-like agent running in the background all day; cannot be stopped.