In the public world this is usually no problem. The first time you used google I bet it was awesome, but that's because it had been running for several years. No one forced you to use it, you used it because it was already good.
That never happens with websites you're required to use. Corporate intranets. College registration systems. They all suck and make everyone's lives miserable for several years before we all get used to them or minor improvements make them tolerable... that's how I feel healthcare.gov is just destined to be.
Google and facebook are designed by website people, who want to make a great website to attract you. If you don't like it, they know you'll go someplace else. There's competition.
Required websites are made by politicians or business people or school principals who have a budget to think about. If you don't like it, their lives won't really be that much worse. And they don't know anything about websites anyway, because you don't get to be a president or principal if you start with a human factors or computer science degree. Those people are on the other side of The Divide, you talk to them hoping that they'll just do what you want with as little interaction as possible.
We live in a country where you can say "I hate math" and get high-fives in a bar, everyone relates to you, there are math "people" and non-math "people" and the two should not meet. It's sad, but that's the way it is. And that's why we are destined to encounter two very distinct categories of websites: the good ones, and the ones we have to use.