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In my humble opinion, the most crippling problem with building complex social websites in Drupal is the frustrating inability of most modules to work together nicely with user relationship modules, as well as the near total lack of support for any kind of individual, user-controlled privacy settings. I'm not exempting my own modules from this: my Facebook-style Statuses module has an architecture that inconveniently prevents it from working as well with user relationship modules as I would like.