get_close_matches is such a godsend. I've already used it this morning to deal with matching up 2 lists with about 100 things in each.

One trick I've found is to use it in both directions and then only using results that agree both ways.

Something like this (very terse version):

    closest_or_none = lambda l, options: (difflib.get_close_matches(l, options, n=1) or [None])[0]
    dir1 = [(l, closest_or_none(l, list2)) for l in list1]
    dir2 = [(closest_or_none(l, list1), l) for l in list2]
    one_to_one = set(dir1).intersection(set(dir2))

Interested to hear how you approached the rotation thing.