Random and continuous stream of directory content

[leupibr]

I have an application that updates videos in a directory and several clients display these videos with a browser (HTML5/HTTP). Now I would like to change this to a multicast stream to reduce the network traffic.

It should work like this:
VLC picks a random file from a directory and streams it. When the stream has ended, it picks again a random file and streams this content. During the stream, it can happen that the content of the directory changes.

Is this - or something similar - possible?