The whole reason why the HTML world took off while the existing technologies lingered is that amateurs could grab whatever they could and run with it - incompetence be damned ! Innovation often happens when amateurs find accessible technology and bend it in strange ways that make the professional cringe. Professional are then needed for security, scaling, cost reductions and all the things that require maturity but instead of innovating they would have refined the state of the art to new and still stagnating levels of perfection. Hurray for amateur enthusiasts who do interesting new things because no one told them it was the wrong way to do it !
I agree. Many underestimate how the lack of strictness helped early users. You could start with plain text and add a few <br> or maybe a <p> (wIthout end tags) to create paragraphs.
Anyone with minimal knowledge could start sharing content. If they had to pass any kind of validation, many would not have bothered. Yes it was a mess, but it helped us get enough information to reach critical levels. I would rather have a web with messy HTML than FTP servers filled with Word documents or a proprietary AOL / MSN
The thing about the web is that it was for amateurs. Things like separation of content and style are great for engineers creating larger-scale maintainable sites, but they're absolutely not helpful for new users. Being able to take a text file and add a couple of tags around some text you want to emphasise is a positive advantage for such individuals. It rewards small experiments. Understanding CSS is, by contrast, quite the undertaking.
Hypertext had been around for quite some time before the web, and there's still some academics I know who seem to scratch their heads at the success of such an simplistic, impure form. To me, its simplicity is a reason for its success, while projects like Xanadu make a fundamental error in not considering enough the importance of barrier to entry.
That last sentence reminds me of a quote from Ivan Sutherland:
When asked, "How could you possibly have done the first interactive graphics program, the first non-procedural programming language, the first object oriented software system, all in one year?" Ivan replied: "Well, I didn't know it was hard."
