Thanks for all your work on this.
Here's what I tried, I'm going to try a test cut today to see how well it works.
First I drew a box around the text I wanted and made sure that the text was centered inside the box. Then located the text on the 'male side' with the text upside down reading left to right.
Next I copied the plane, jet stream and text in the box and pasted them to the "Pencil Box - Take Flight.crv". And put them on a new layer with a new color.
Then I flipped the text over and made sure to recenter the text inside the box.
Next I mover the plane, jet steam and the text over the plane and jet stream and made sure they overlap each other.
Then in the layer for the imported text I deleted the plane, jet stream and box, leaving just the text.
Then I 'Calculated' the "V-Carve - Plane and Line" making sure to select the plane, jet stream and text.
I think this will work.......