One of the things about the Riemann Hypothesis is that the search space for a proof is more wide than it is deep. For each given idea or approach it doesn't take relatively long to get to the forefront of what is known, and an expert can often tell you right from the beginning that the whole class of approaches may not work due to some known phenomena, or that they would have to involve certain complications to not pick up on various almost-counterexamples. Furthermore, in these 150 years not only has the right path/approach not been found, but there isn't a truly compelling reason to believe that RH is true, aside from numerical evidence and a belief in beauty.
I think it'd be fascinating to put together an online resource to organize the possible approaches, list the knowledge prerequisites, show the potential counterexamples and stumbling blocks to each approach. This would help anyone interested in the problem, and once it is sufficiently developed it would allow non-specialists to contribute productively. This could be LaTeX on github, it could be more of a traditional wiki, but now I really want to get this going.