If a plain list has more than four levels, org-mode will produce latex that crashes. See attached. On the other hand, html export works fine, even for much deeper lists. In a large org file, this export error is pretty time consuming for a naive user (me) to isolate, so I'd like to suggest that, before crashing latexmk, org-mode should at least print a human-readable warning -- especially since deep list export works for other export types. Better yet, would be deeper latex lists. There are ways: http://tex.stackexchange.com/questions/41408/a-five-level-deep-list