Seems to me that you can project your texte like a real wraping with the function Construct /Curve / project :)
In some action
project up line curve of the letter on one cylindric surface
project down curve line of the letter on one less cylindric surface
reconstruct the letter
Make boolean Cylinder / new letter = your real wraping text :)

Here you have just make a "straight" projection not a "rotative" projection :)