This is an example of the fun stuff I get to do at work... Our contentent editors use Adobe's (formerly Macromedia's) Contribute 3 to edit content on our website. Ever few weeks I get a call from an editor saying that they can't edit their page any more.
After a little investigation I find what Contribute has allowed them to do. Apply dozens and dozens of nested font and bold tags around single links, images, and text. Some of the nested formatting is only applied to a single character such as the number 5. Why Contribute isn't smart enough to handle this I don't know.
Another question is why Dreamweaver's built-in "clean up HTML" function croaks on the code it's sibling product created. The error message displays something to the effect of "too deeply nested".
So if Contribute is going to allow people with no knowledge of HTML, or at least, not give them the ability to even edit the HTML then Contribute should take the responsibility of assuring that this crazy nested formatting doesn't take place, so website managers don't have to fix problems like this only after 5 or 6 updates to a page.