I've downloaded Silverstripe a couple of weeks ago and really liked it. I've even presented it in the office and we were all very excited about it, to the point that we decided to test it on a real project.
Everything went smooth while developing localy as permissions are more loose, but when I tried to upload the site the problems started.
Aparently Silverstripe is extremely reliant on some php features that not all hostings have or make available to the user. One simple example of this is the $_SERVER['SCRIPT_FILENAME'] variable not being available or the many write permissions that need to be enabled in order for Silverstripe to install and work properly.
I see real future in this CMS, but it needs to improve a lot on supporting different eviroments like many other CMSs out there have, like Wordpress or Drupal.