Yes, once. Our research lab’s in-house software suddenly started throwing segfaults. The update was from the Mac side (OS), not the software side, so it would’ve been near impossible to figure out exactly which feature of the software no longer played nice with the new MacOS. We (me and a mentor) used git bisect to figure out what feature didn’t work, and patched it for the new OS update.
The next week I went and bought a new laptop and installed Linux on it so that didn’t happen again.
I used this book to teach a course. It definitely encourages you to think of programming as a means to an end, and not a skill in and of itself. That is completely fine IF that is what you want, and from your post, it sounds like it is.
If you find you’d like to dive a little deeper, I enjoy the Think Python book as a more “mathematical” and “rigorous” introduction. That doesn’t mean it’s harder. It just means it has a different approach and end goal!