Assuming I’m advancing patterns live and not programming the Arranger, does a new pattern always begin on step 1? I’d like the playhead to sync globally regardless of pattern changing if possible. Thanks!
Hi, in my manual in chapter 12.10.1 you will find the switch for pattern vs. project chain behaviour.
Settings for the pattern chain behaviour: 8.6.3 Sequencer
Further readings of interest could be 12.14 Scale Setup 
Hope that helps a bit!
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Unfortunately, the solution posted by @gerkinear will allow you to specify when a pattern will change, but the subsequent pattern will always start from the top.
On the A4, what you are asking for is called direct jump (and its a brilliant feature), but I don’t know if the OT has an equivalent. Maybe someone with a bit more knowledge than myself can chime in here?
Honestly I don’t think it’s possible with the OT that way.
You could sample 2 Pattern, and edit them on the fly if you are fast, but that could lead to fails.
I have a workaround that can be used for direct jump type behaviour (just on one track).
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So you copy the pattern with the fill. Then move back to the main pattern and just Paste (to play the fill pattern in time with the sequencer as direct jump) and Paste again to undo and play the unaltered main pattern. Is that right?
Yes except the term ‘pattern’ wouldn’t be strictly correct in OT usage. The thing you’d be pasting/unpairing is called a page (that is, 16 steps of one track’s pattern)
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What button combination do you press to do this “page” copy/paste? On which screen do you have to be on? Thanks again! 
Grid Recording mode, Scale button + Copy / Paste
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Couldn’t you simply use the FILL function? Does it not work with MIDI or something?