Now that’s odd. I just looked into the code at http://hg.python.org/cpython/file/2.7/Lib/shutil.py#l103 and there is a guard against EOPNOTSUPP:

try:
   os.chflags(dst, st.st_flags)
except OSError, why:
   if (not hasattr(errno, 'EOPNOTSUPP') or
   why.errno != errno.EOPNOTSUPP):
      raise

Does your /Library/Gentoo/usr/lib/python2.7/shutil.py look the same? Would you mind adding a `print why.errno` just before the raise?

I have tried move'ing files to NTFS and FAT32 and it works just fine here.