### Update 0:07 1/14/2020 Didn't test the tests. I was checking the opposite of what I wanted, which resulted in switching the functionality of __gt__ with __lt__ (kind of). It's since been fixed (although the SO question was also answered, so this code can probably, safely be ignored)

from typing import Iterator
from unittest import TestCase


class ILengthComparator:
    def __init__(self, iterator: Iterator):
        self.iterator = iterator

    def has_more(self) -> bool:
        try:
            next(self.iterator)
        except StopIteration:
            return False

        return True

    def __eq__(self, length: int) -> bool:
        if length < 0:
            return False

        if not self.has_more():
            return length == 0

        return self == length - 1

    def __gt__(self, length: int) -> bool:
        if length < 0:
            return True

        if not self.has_more():
            return False

        return self > length - 1

    def __lt__(self, length: int) -> bool:
        if length < 1:
            return False

        if not self.has_more():
            return True

        return self < length - 1


class TestCmpIterLength(TestCase):
    def test__eq(self):
        test_inputs = [(iter(range(10)), i) for i in range(-5, 15)]
        expected_outputs = [10 == i for i in range(-5, 15)]
        actual_outputs = [ILengthComparator(test_iter) == test_length for test_iter, test_length in test_inputs]
        self.assertEqual(expected_outputs, actual_outputs)

    def test__lt(self):
        test_inputs = [(iter(range(10)), i) for i in range(-5, 15)]
        expected_outputs = [10 < i for i in range(-5, 15)]
        actual_outputs = [ILengthComparator(test_iter) < test_length for test_iter, test_length in test_inputs]
        self.assertEqual(expected_outputs, actual_outputs)

    def test__gt(self):
        test_inputs = [(iter(range(10)), i) for i in range(-5, 15)]
        expected_outputs = [10 > i for i in range(-5, 15)]
        actual_outputs = [ILengthComparator(test_iter) > test_length for test_iter, test_length in test_inputs]
        self.assertEqual(expected_outputs, actual_outputs)