I think I feel a bit like your friend: web development is not supposed to hurt that much, and it usually only happens if you start doing things in obscure ways,

I think I feel a bit like your friend: web development is not supposed to hurt that much, and it usually only happens if you start doing things in obscure ways, or unusual environments, or whatever else. Unfortunately, when you're just starting out, or trying something as a hobby, it's difficult to tell what the "correct" way of doing things is, so beginners often fall into these sorts of traps. I don't think this is any different with web development, GUI programming, machine learning, embedded, or anything else. I did a bit of work with Pandas recently and spent the whole time going "but this is so dumb - why would it work like this?" In reality, it was not dumb, I was just inexperienced with the task and tools I was working with, and was running into problems because of that inexperience. There are some ways to mitigate this, and good learning resources that show you how to get onto the happy path (without bombarding you with too many best practices up front) are worth their weight in gold. But I think it's very easy to forget what it feels like to learn something new, so often when we approach a new area of programming, we notice how difficult it is to learn, and that feels surprising to us - even though it surely took us a long time to get comfortable with the stuff we already know.