Depending on how you feel, being a utility guy that runs an OT and a guitar and keys is a pretty cool position in the band. Liam Hewitt isn’t the front man of prodigy even though he does “all the important stuff.” Perhaps lessening your load so you have the ability to focus on driving the whole show with the OT is a possibility. Play other instruments when you need to. But you know your arrangements better than I and can judge whether that’s possible.
Nearly all the same issues are there with Ableton, just a different flavor of issues.
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Another couple of thoughts while I’m just thinking about it:
The potential downside to the plays free method is that you need to choose which section you want to loop beforehand, though it sounds like that’s what you were intending to do anyway?
There’s some ways to do slice loop selection on the fly though I think, for example because the start parameter only takes effect once you trig a sample you could use the scene crossfader to select the slice after you start playback. But that’s some extra manipulation you’ll need to do live and will prevent you from using it for other cool and fun stuff.
You can also just manually trig whichever slice using a foot button and keep the length to 1, only changing it to the max when you’re ready to play through the rest of the song. The quantised trig thing in the attributes page should sort out the timing for you. This would also require either using the crossfader or setting up something on the foot controller to deal with setting the length parameter.
But stick with it, this will take weeks/months/years to figure out and master. It’s worth it, there’s nothing quite as flexible and powerful as the OT for this kind of thing AFAICT.
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Definetely POSSIBLE ! And simple. Can be 1 button.
Why wouldn’t it be possible to send Program Changes ? 
Slice aren’t necessary, but they save slots though.
If your loops are 4 bars long, I’d recommend Recorder + Flex instead of Pickups for live looping.
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Worth mentioning this very useful tool for exporting your song sections as a pre-sliced file for the OT -
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