It makes a person want to start over, from scratch while keeping it simple adding as little as possible. Of course something like that would have to be done extraordinarily well to be worth it at all to avoid https://xkcd.com/927/
There isn't an intelligence capable of designing big open standards like the web, rather they only move forward by natural selection, much like terrestrial life has.
In the end I think we've gotten some pretty remarkable things this way, remember before the web there was no such thing as cross-platform, instantly-available globally, and accessible to any person with any disability multimedia. Few people seem to recognize how much of an accomplishment this is: http://www.youtube.com/watch?v=uEY58fiSK8E
I think the problem here is big.
How about small standards with a limited scope? I don't want these huge standards that take millions of lines of code to implement.
Again, the point is it's too big to be designed.
In the process it's degraded pretty badly as a document delivery system. If you start over I recommend separating those two projects.
And then people were making websites entirely in Flash.
And then people realized that was a bad idea because Mobile, and everything got better.
Until the App Store came along. Fine, so now program delivery has been separated from document delivery, but every document provider that used to just be a website now requires you to use a special program from the App Store instead of using a web browser or some other generic "document viewer". Or, at the very least, you have to tell them you don't want it every time you visit their website.
The problem isn't that the web is a bad document delivery system -- it's not. The problem isn't even that the web is just as good at delivering programs as it is at delivering documents. The problem is that there are a large number of people who know nothing about best practices and are way too enthusiastic about making things look flashy. They create documents and they don't care how you want them to look. If that means they have to create a Program instead of a Document, that's fine with them.
(Accept)
Well let's see if we can make a short list:
1) Can I look up almost anything? Yes [0]
2) Can I learn a foreign language for free? Yes [1]
3) Can I fund something interesting? Yes [2]
4) Can I communicate with my family and friends for free? Yes [3]
5) Can I learn stuff for free? Yes [4]
Seriously I didn't even try, yes progress has got us somewhere. Admittedly we do now have n+1 standards
[3] Honestly there are so many - email, skype, facebook, whatsapp, etc ...
edit - edited
And your 4) we could do that in the 90s as well. Email isn't a 21st century invention and doesn't depend on web technologies. Same with instant messengers. Skype - for video, bandwidth is the thing the 90s lacked to support this system. WhatsApp - widespread mobile devices was necessary for this, 90s lacked that. And none of them, other than Facebook, is wholly dependent on web stuffs, they're internet technologies and platforms.
Indeed all those sites mentioned are just manifestations of an idea that is really independent of any "progress in web standards", and had someone thought of the idea 20 years ago, they could've just as easily (or maybe even more easily - because of the relative lack of complexity back then) set up a site for it.
Well, I know your 20 years is hyperbole, but let's see:
1) We can display video and play sounds. We can do it using native browser controls now, but in 1994 you couldn't do it at all - plugins weren't introduced until Netscape Navigator 2.0 which came out a year later.
2) We can display updated data without reloading the entire website. This let's us do stuff like chat or use collaborative tools.
3) We can disassociate content from styling, so styling data can be transmitted once and can be changed en masse with ease.
4) Cookies showed up 19 1/2 years ago, so you wouldn't be able to store user login data without it showing up in the URL - it makes sending URLs to other people very awkward.
5) Oh wait, you wouldn't be able to log in because forms weren't in the HTML spec yet, HTML 2.0 didn't come out til 1995.
6) We can actually... do layouts of web content. Tables didn't come around til HTML 3.0.
The initial version of the web was pretty much a prettier version of Gopher - with some inline graphics and styling. This site in would not be able to exist in 1994, unless you wanted to submit comments via email?
Having said that, it's possible that we might be in for a second era of webdesign, as MS retire support of XP and the browsers that have dragged down web development.