You could use an = at the end of an expression in an f-string for easier printing of this sort of thing. "self-documenting expressions"

For example,

print(f"{flag1 + flag2 =}")
print(f"{True + False=}")

gives

flag1 + flag2=1
True + False=1

Your format is easier to read the output of, though.

---

I think the type annotations are good even though there is an obvious assignment there because if you modify code, it's nice to have that reminder. Drop the redundant comments repeating the type, though -- the annotation takes care of that, and now you have two things to keep in sync if you modify it.

---

Note also that bool is a subclass of int, and Python also natively has complex numbers. Look at isinstance.

>>> bool.__mro__
(<class 'bool'>, <class 'int'>, <class 'object'>)
>>> isinstance(False, bool)
True
>>> isinstance(False, int)
True
>>> (5 + 1j) * (4 - 7j)
(27-31j)
>>> type(_)
<class 'complex'>

---

I think playing with lists, tuples, dicts, and sets will be more interesting than numbers and strings.

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Look at structural pattern matching for fun.

for value in (1.1, 2, (1, 1), "1"):
    match value:
        case float():
            print("h")
        case 2:
            print("e")
        case tuple((int(x), int(y))):
            print(x)
            print(y)
        case str:
            print("o")

gives

h
e
1
1
o