>Is there a reason not to use metadata? Doesn't it make the web easier to index, and therefore easier for everyone to use?
Yes, there's a very good reason not to use metadata: it's extra work, and it's not very fun, just like writing docs for software. So people don't want to do it because it isn't "sexy" (and there aren't very good incentives to overcome people's reluctance to do that work).
Because of this, just like any job that people don't really want to do, you have to "bully and cajole" them into doing it.