The Web can continue to evolve by taking the long term view and chipping away with adding necessary functionality, and eliding some of the mistakes (albeit hard).
Evolution is resilient and special. Pair it with immense time frames, and life will find a way, even as many experiments will be left on the way side. One of the strengths of the Web is how it evolves as a platform, but it can be a double edge sword.
We can’t expect to constantly evolve while keeping the entire history front and center. We have fragments in our DNA that go back to the birth of life, but much of it is very much hidden and ignored.
We can embrace evolution that allows us not to keep the baggage around. If you look at a hello world web app, that supports a decent set of browsers, you will find yourself setting up resets of sorts, meta tags, and a series of cruft. This cruft creates cognitive overhead for developers.