When extruding text with draft, the whole process with a sentence fails when a letter has a hole in it, like R, O, P, A or when the draft is too high that both sides of the leg of a letter would overlap it each other. It brings up the error: "ACIS error: Rigid sweep with draft". I don't mind if they would overlap.

Is there something I can turn off so that it allows me to overlap the draft? Like you can do Pipe options, "Allow Self Intersection".

Using ViaCad 8 2D/3D (9 has still too much bugs to be functional) and Mac OS X Yosemite.

Try converting the text to curves from object type than do each one individually. There's a limit that draft can do with letters until wall will start to collide. Maybe doing it individually avoids the error.