Transition / Cut Advice for Video Idea
You could use black screens as section dividers, e.g. one screen could feature a large question mark and the other one an exclamation mark as text.
The idea is to drag the black screens across the video frame from side to side at the same speed you're panning. Make the animation so that it looks like the black screen is attached to the middle pole.
Step by Step:

show the black question screen for a second or two
cross dissolve to you asking the question, the camera being fixed on you
begin panning
as soon as the pole comes into view, move the black answer screen from off-the frame into view, at the same speed as the panning, so it looks like the pole drags the screen with it.
this screen will cover the empty lift seat while you pan
the black answer screen comes fully into view
in the background cut to the other video track
Cross dissolve again and show you sitting in the other seat and answering the question.
start panning again
and so on

You could start the speech tracks just before the dissolve effects start, this is a common technique that simulates typical human dialogue where we perceive someone started speaking first and only then turn our eyes on that person. Research J and L cuts if you want to know more about this.
Also record some ambient sound from the lift ride and environment, that can be played continuously on loop in the background.