Hi!
I just installed SilverStripe for the first time and wanted to give some feedback. I guess this is not the perfect place but unfortunately I couldn't find anything else to give feedback. So this is my first thing: Give people a way to give feedback.
The install process went smoothly and I could find all the information I needed. It was also very easy. But I had one usability issue with the layout of the installation screen. I was not sure about the "steps", where I was and what would be next. Major confusion was the placement of the button to proceed which is somewhere at the top but not at the very top of the form/page. I scrolled down to read and check everything and I expected a kind of "next" button at the bottom.
Second, I don't like that it is recommended to remove the install dir after the installation process. I think that it is a problem if you want to put your source tree under version control, for instance. There are a lot of similar web apps that do this smarter (i.e. Drupal).