How can one "Insert silence" in session view - to the loop itself?
(Guess there must be an easier way than re-recording).
Okay, how about this- not for LONG silences, but it kinda works. When you want to insert silence, first set the "end" time so that the loop is now longer by the amount of time you wish to insert. For a 2 measure loop (1.1 1.2 1.3 1.4, 2.1 2.2 2.3 2.4) if you want to insert 2/4 of a measure you would change the End value from 3.1.1 to 3.3.1.
If it won't let you adjust the end point, click the warp button off, then back on and it should let you.
Then Make a warp marker where you want the silence to be inserted, and another one a bit before it (about as far as the length of silence you wish to insert)
grab the warp marker at the point you want the silence and drag it as far as the amount of silence you wish to insert.
Then use the draw tool to draw the volume envelope to zero (mute) where you want the silence inserted.
Got that? Kinda silly, but you can always just take it into the other view and do it; Ableton 9 has a consolodate back to the other view now that makes it a bit easier.