Note: I was told at StackOverflow this question would be better here.

I have tried to learn various programming languages, but never really got invested in it. This is because I cannot estimate how much skill is necessary to do a particular project.

Whenever I start learning a programming language, the first things I always learn about our lists, numbers, floats, strings, etc. I've used these for example to code a one-time pad in Python. I've also use HTML to code forms and know enough to parse them and extract data for storage in a database. But I have trouble moving beyond simple programming tasks. It's usually stuff involving lists, numbers, and data entered in simple inputs. One outlier in this regard was Pong. Pong was one of the first simple yet interactive things I ever learned how to code.

My question: What are some good resources that can explain how to decide how complicated or elaborate a programming project will be before attempting to do it?

I feel like if I could do this, I could better assess what's realistic given my skill sets and set projects that are doable for me.

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