In a blog post by Serge Wroclawski, a long time OpenStreetMap contributor and the founder of the OpenStreetMap US organization, outlines reasons why he believes OSM is in trouble. 

A choice quote.

"The first problem that I feel plagues OSM is that the OpenStreetMap Foundation views the mission of the project to provide the world a geographic database, but not geographic services."

See also this thread on the OSM-talk mailing list: