95% of the information on the web is written language. It is only logical to say that a web designer should get good training in the main discipline of shaping written information, in other words: Typography.
Building structure requires serious listening, serious reflection, and serious imagination. All this requires experience, and no matter how experienced you are, it costs you. We spend our time and nerves to save users their time and nerves. Well-designed things give us the invaluable present of time. Well-designed products do not just save us time, they make us enjoy the time we spend with them. They make us feel that someone has been thinking about us, that a nice person took care of the little things for us. This is mainly why we perceive well-designed things as more beautiful the longer we use them, and the more used they become.
I think part of the difficulty in allowing ourselves to properly delight in the imperfect, comes from conflating delighting in something with wanting it to happen. This isn’t the case. You can appreciate something as it exists while acknowledging its problems. You can see that a fire is beautiful without becoming a pyromaniac, and you can appreciate the absurdity of your political situation without thinking it’s good.
Even if a delight in the imperfect causes you to want more imperfection in your life (and it should), there is no shortage of imperfection to seek out. The imperfect is not scarce, it’s abundant. If you find imperfection delightful, you will never be short of things that delight you, even if you fix any given problem. Solving problems and smoothing out imperfections doesn’t remove the source of delight, it merely opens up new vistas for it. You could give yourself over totally to delight in the imperfect and never run out of things to explore, even without creating your own.