What is the biggest challenge you see with getting press coverage?

Personally i haven't tried to land media coverage and therefore just can imagine what the hurdles are and tell you what my perception is: My first thought was kind of the same as looking for a partner: If you are looking for one, you ain't gonna find one. :D I think this is the same for getting media coverage. If one is trying despirately to get covered, it will not happen. On the other hand, if your product is (marketed) interesting or useful enough you will make noise and waves and media probably will notice you as well. So in the end i think best is if you let media discover yourself than trying to land it. This way around you also have already another market validation. Kind of messy thought process, but i hope it helps anyway. :D