From what I understand, in adamfolio’s situations:
says, /Wordpress/wp-content/uploads/2008/03 cannot be created. And the “parent directory” include wp-content, uploads, and 2008.
if your system exist WordPress/wp-content, and there is no any subfolder under wp-content, then this folder is the parent directory, and should set to 777.
if your system exist WordPress/wp-content/2008/02, and the wordpress is trying to creat WordPress/wp-content/2008/03, which mean the folder should set to 777 is 2008, instead.
hopefully this will help
regards,
cilipadi