Well, I got my "die-hard" medal for only one spot. It took me like, 300+ pics, handful of video, and some picks. It took a looooong time. You get a medal by how many 5 stars your stuff is rated. So just keep adding and adding, and hope people will rate them high, then you get a high medal.

For example, in another spot, I submitted like 700 pics, some video and 2 picks, all I got for that spot was a "dedicated medal" when I was aiming for a "die-hard medal" but since some people rated low or not at all, I got a "dedicated" medal.