Looks like something weird happening in this case, note that the indices of the second text span are incorrect:
>>> seg = pysbd.Segmenter(language='en', clean=False, char_span=True)
>>> seg.segment("1) The first item. 2) The second item.")
[TextSpan(sent='1) The first item.', start=0, end=18), TextSpan(sent='2) The second item.', start=0, end=19)]