Hi Suzi,

About your first question - yes such scenario could work, you can also look at this:

http://forums.autodesk.com/t5/autocad-for-mac-general/help-new-mac-autocad-15-no-printer-and-can-t-g...

About the issue with CTB file from Windows: which output size is on Windows side? Is it the same as you tested on Mac (11 x 8.5 paper)? Or it is bigger?

Could you attach here example DWG file with accomplishing CTB file? (it is better to compress them in one archive before attaching).

Maxim