This has been one of my peeves for years. Apple is capable of good design, and overall is well regarded for it, but there are a number of places where they have blinders on and absolutely refuse to fix extremely obvious missteps.

You say good. I'd call it minimal. Minimal doesn't mean good.

For example, I have bold text, larger text. On my mac I have all these contrast increasing settings enabled, simply because it's *not* good "design"

It's good that it's minimal, but this minimalism is also why many things don't work (timemachine, icloud files/photos -> everything needs to be automatic, causing recurring downloads follewed cache eviction of those files). Etc etc etc

Apple is capable of beautiful and minimalistic designs, but their usability has been terrible since basically the iPod.

Minimal is often an enemy of usable.