I got a call from a guy saying "hey, this broke". I had not touched this system in 13 years. I had to re-remember a bunch of stuff. Some of the code was still a joy to work with. The parts that were hard were... obvious, and even then, I remember cutting corners, not documenting stuff, and overcomplicating things "just in case" (which mostly never happened).
There's little amount of someone 'telling' me ahead of time how much difficulty I was leaving for the next person (or even myself). It really seems like the only way to get this experience is with time. That doesn't mean you can't follow some best practices that turn out to be beneficial. But until you've experienced the downsides, you won't really be able to internalize the why regarding something being good or bad.