In answer to your second part:
It's true that all non-zero integers are "Truthy" but this does not mean that 5 == True will return True. The == operator is comparing value and, when comparing values, 5 is not equal to True. If you compare bool(5) == True then that will return True. When you do if 5: what you actually are doing is if bool(5):.
The reason that 1 == True returns True is that in Python the boolean class is a subclass of int, with True being represented by 1 and False being represented by 0. So 1 == True returns True because they are equal.
Note that, as discussed in this question, this is NOT GUARANTEED in Python 2.x as True and False can be re-defined. In Python 3.x they are keywords which will always be equal to 1 and 0, respectively.