Installed and configured CafePress module. Accepted the default image directory, images/cafepress. Added the CafePress block to the right sidebar. Saw many error messages like these:

# The selected file /tmp/filejvspLi could not be uploaded, because the destination  is not properly configured.
# The selected file /tmp/file3lbukg could not be uploaded, because the destination is not properly configured.

Examined cafepress.module and reviewed Drupal API code for file_check_directory function. Noticed that file_check_directory calls mkdir without specifying a recursion parameter, thus accepting the default, false.

Reconfigured CafePress module with the single level image directory path, cafepressImages. Reloaded front page and saw my CafePress products. Excellent!

It is possible that the default image directory, images/cafepress, worked for the developers because they already had an images directory and only one additional directory level was needed.