Hi Lucas,
My apologies for the delay here. I'm finishing up a few videos that answer your questions and demonstrate how to do it.
Yes it is possible and easy to calculate and report on overbreak/underbreak volumes in the TBC tunnel module.
As for creating a cylindrical surface, in v4.10 we can create a radial surface from surveyed points, and in TBC v5.0 we can create meshes from point clouds and report on volumes from those meshes compared to design.
Let me know if you have any other questions, I will post a link to the videos once they are on YouTube.
Matt