There are tools that I’ve used occasionally for many years that I’ve just started to appreciate lately. “Oh, that’s why they did that.”
When you see something that looks poorly designed, don’t just exclaim “Why would anyone do that?!” but ask sincerely “Why would someone do that?” There’s probably a good reason, or at least there was a good reason at the time.
If something has lasted a long time and has a lot of users, the designers must have done something right. Their choices made sense in some context. Maybe it wasn’t designed for you and your needs. Maybe you’re not using it as intended. Maybe the design made sense at the time but the world has since changed.
Technologists are bad at conveying motivation. We document, or reverse engineer, the what, but the why is much harder to come by. It’s not something people like to talk about.