Thanks in large part do other folks (well, mostly Nathan) who dug in and figured out the private API to enable this in WebKit, we can actually use the web inspector from the desktop Safari browser to investigate pages we are viewing on the iPhone simulator. This has been huge when I have a strange bug in the layout of a page on the iPad and can’t easily determine which element it is.
Here is my version of the script that takes things a bit further:
Since I use chrome as my default browser, I quickly found that the remote inspector didn’t always work with it - so I open safari automatically and load the inspector. Just one less step to worry about. I wanted to have it open the simulator and run Safari as well, but that turned out to require other tools to be installed so I punted. This is really the most common case for me anyway.
If you want a copy locally I recommend grabbing the one from my dotfiles, which I will keep up-to-date if I make any tweaks and changes.