At the moment loop is a one time thing so you have to press it again to make it loop each time. However this is something I raised with Matt a few weeks back and he said its already on their list to have the option of setting it to keep looping until you turn off loop.
Not sure exactly how it will work whether it's a new button or a preference to set but either way it is being worked on.
So for now just keep pressing loop each time but repeat looping is on its way.
I'm sure one of the LC guys can chip in with any more detail.