This is awesome. I work in Live too, and sometimes I will record four separate tracks with synth melodies in the lower-mid, mid, high-mid, and high frequency zones, and I record each as audio out from my midi-sequencer going right into my audio interface. I usually stop recording each track at a different point, though, so say one of them lasts 17 bars, another one is 16.5, and another 18.25, etc., and when they all play in loops they end up restarting at different points and some happy accidents ensue kind of like how you say here.
I use an MPC live for sequencing drums and my synth, and the problem that you are trying to solve here with triggering clips could most likely be done very easily with the MPC live, which integrates with DAWs (although I have never used it this way). The Live has something like 128 tracks per sequence, so you could definitely get the kind of thing going by recording in your DAW and then drag-n-drop your clips into the pads on the MPC. I think someone else mentioned the Ableton Push too, which is probably even better for doing something like this. The MPC has the advantage of working well without a computer, though.