So my friend says he has the settings unblocked to allow downloading items and dinos, however were still unable to get this feature to work. Please help?

As far as i know you can only upload and download from cluster machines.

@Elusive Jester - You must Un-Cluster your servers (if clustered) to allow the upload/download of items/dinos/survirors from other servers - the re-cluster them when your players are finished. (This is what I had to do with mine!) HTH