I see your point about the text widget... I'm using about 4 and 9 is quite a lot, but if you like dividing your sidebar into different sections, I can see how you'd go through the 9 quite quickly. You can separate some of your content by using
<br>, particularly if it's just clusters of images, but if you're using them for your blogroll. etc, that wouldn't work. Maybe having an option to upgrade to more widgets would be useful (like we can purchase an upgrade to the space allowance)?
As for contacting support, it can be a problem sometimes; I live in Australia, so it doesn't usually open here until about midnight. On the whole I haven't had many problems with WP, though, so I don't mind staying up late occasionally to send a support message. And a lot of the other problems are handled in the forums, which staff do monitor as well. So I don't think there's a way round it, or at least not until Automattic expands; and if they do, it might not be the same service we have now. If you can't get through to support, maybe you could start a new thread in the ideas forum; that might be the next best thing.