Drupal's user experience and interfaces got a lot better with Drupal 7. Still, there are a few areas that need work.
One of those areas is the process of adding blocks, configuring them and placing them on the desired pages. Here are a few thoughts on how to make it a better. Please note that those drafts currently don't consider all use cases around block, it's more like a starting point and I will probably add scribbles in future.
Adding blocks "in place"
The story starts when you want to add a "new" block to the system. Usually you already know what you want to achieve and where you want this block to appear. But using the core interface you have to navigate all the way to the block admin page and then click "add block". Instead we could have a little toggle item in the toolbar (or somewhere else) that enables the block in place interface.
Never mind the colors, it's just a raw draft. Once enabled all regions configured to show will have a frame and link inside. If you click on the link the dialogue pops up and you can choose which "kind" of block you would like to add.
For now we'll simply choose "text block" and continue in the wizard.
As you can see the process of creating the block and the actual settings for displaying the block are not thrown together on one screen. Also when choosing where to place the block you can either choose a pre-defined context (which will cover most complicated use cases), choose the URL (just like Drupal core does it now) or even leave the default setting which suggests to place the block on the very page that you've started your wizard.
The idea is to make the whole thing much more contextual. You are on a page in your system and you think "ah - let's add a box here". You click, create your box and save (the rest of the wizard is friendly towards this decision).
The wizard completely eliminates the pain of "configuring" a block placement and makes use of pre-defined contexts (while it's usually a developer's task to maintain contexts).
If you choose to add a views context - instead of going to the views creation page - we would allow users to select pre-defined views blocks. At a later stage it could be also possible to allow users to create views along this process but for now the idea is to make things simpler (and views is rather complex).