Just got the trophy. Here is some info that should prove helpful for others trying to get it. Although it doesn't have to be downloaded by different PSN users, downloading the same content 5 times doesn't work, all the same PSN ID downloads count as one. But different content counts as a separate download so you can just have 5 pieces of content and the same user downloads them. Just make 5 logos or 5 finishers. Use the Content by this user function and you can find it all quite quickly. Keep checking the Community Creations using the Download option, it pops the trophy after checking your User Prestige.