2 Puppets 2 separate recordings

If you want two characters to have a conversation that goes backwards and forwards, drop both characters into the timeline, adjust their Position X in the Transform behavior (so they are not on top of each other), and Scale in Transform (if too big for the screen).

Then select (in the timeline) the first puppet and record its first line of dialog, then select the second and do its line of dialog, then go back to the first and record its next line of dialog, etc. I do it this way rather than recording all of the first character dialog then all of the second character. The reason is it allows you to move things around more easily on the timeline. E.g. if you don't like one of the takes later during review (e.g. you want to add some more words), just delete it, re-record that part, and move everything else around on the timeline to make it fit. If it was all one recording for the first character, working how long to pause can be tricky - and its hard to adjust later.

I start with the dialog to get override timing right, then I go back and enable draggers, triggers and add them later. I like doing the full scene crudely, kind of like storyboarding, get a rough feel, watch the whole sequence, then refine and improve it. Is the timing right? How do I think head tilts should look? Is the composition good? Its not required, its just the way I like to work. Refine, review, iterate. You can enable each behavior separately to record them one at a time - I normally do multiple passes for draggers for example, do the head movements first, then do the hands, etc. I don't do crazy small recordings, but I do avoid recordings that are *too* long to make things easier to reposition or extend / trim in the timeline.

But there is nothing to replace practice and experience!