I want the top squares to fit around the odd shaped circle, at the same time be able to edit them as if they were in a straight row and have the edits pass down to the squares around the oddly shaped circle. I know smart objects would help in solving, the warp tool is not precise, liquify too much fighting with.
So do you want the rectangles to curve also? How aobut just one rectangle in a Smart object? You might be able to warp just one at a time rather than a whole row. Or you can try puppet warp.
I'd prefer them all at the same time, sounds like a job for a script, lucky for me I haven't got to that level in scripting at this time.
I think Photoshop is ill fitted for the task.
If the shapes are hard edged anyway an Illustrator »Art Brush« seems a better choice.
This would not provide immediate updating when editing the original elements but alt-dragging them onto the Brush in the Brushes Panel allows for updating the object/s the Brush Stroke has been applied to.
I don't have access to Illustrator, only Ps, hrmm any more feedback ?