The other side of this is also, what happens if there’s an anticipation chord in a spot where the style doesn’t actually have one? How well does the audio streaming change the chord in an area that the recording didn’t?

A MIDI style has the same exact rhythm for all same type chords, all that changes are the notes. There might be a different pattern for major and minor etc., but anticipate with a similar chord type (or even a different one if the style doesn’t change that much) and you won’t get rhythm glitches, or at least they’ll be mitigated by the same portamento codes that help at bar boundaries too.

An audio track is going to rely on the studio player being inhumanly accurate to duplicate the same pattern in all keys. To the point where jumping from one file to the next may introduce a glitch you won’t hear on a conventional arranger.

Audio loops SEEM like a great idea, but in the hands of less accurate players may exhibit problems you don’t come across so much with ‘old fashioned’ arrangers… 🎹
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An arranger is just a tool. What matters is what you build with it..!