So you found the Chords you want to use and drag them to the Main Track. You bind those Chords and record a user track to capture the custom live performance. Now, how do I get the articulations,moods,performances etc. to follow this user track verses having to manually size each chord in the main track to match my user track timing 
Agreed. Having to manually size each chord has been a bummer for me.
Yes no doubt this is one of those quirks that an inherently versatile and new workflow found in Scaler 3 throws up. I also agree it’s laboured. We are working a Chord Rhythm Detection that you can analyse from MIDI or user track. That would be magic. As with every new feature or improvement we introduce we have to be very careful about the other many scenarios various users would encounter. Please stay tuned!