Having never used it before, is it that bad?

Measuring a coastline creates a well known paradox: https://en.m.wikipedia.org/wiki/Coastline_paradox

The problem with recreating cryptographic libraries is that unless you are a cybersecurity expert, you are very likely to leave hidden vulnerabilities in your implementation.

Why am I like this

Welcome to today’s lucky 10,000!

Typing when you need it gives you more freedom over a toggle. You can choose to type some parts of the code while leaving other parts untyped.

For example, if I’m writing a quick and simple Python script I may forgo typing, but when iterating on it I’d go back and add the types I need.

Python 3.x will never have static typing because that would break backwards compatibility.

However, typing hints have been Integrated into Python for a while, and you are heavily recommended to use them, so your IDE can enforce typing.