One problem with MAC files is that the file is split into 2 parts: DATA and Resource Fork. I think R.F. is like a INFO file, which keeps important info about the file. When you copy the file from PC to MAC, the R.F. part will be lost and the MAC will not know what to do with that file.
the best bet is to compress the file on the MAC with Stuffit and then copy to Shapeshifter.
And also you need "DISK COPY" program to mount the images.
I learned that the hard way.