No CMS or CMS like application is going to fit ones needs out of the box. Not WordPress, not Drupal. They will require a learning curve, some more than others (Plone for example). And for certain tasks and/or requirements there may not be a plugin that will do exactly as you desire.
What I would suggest is listing your requirements.Then, going through those requirements while evaluating each CMS noting down how much of those requirements are met. Figure out which CMS fills the most requirements while still providing the most important benefits and features you desire.
For example, the one that fills 100% of your requirements may have a very high learning curve while another, that is close to filling your requirements has less of a learning curve and also has a more active community. Weigh the positives and negatives and decide which of your requirements are most important and which system can provide you with those.
Other items to consider are the community, code base, and the ability to extend functionality via modules/plugins.
That being said, I would recommend Drupal or possibly Wordpress. If those don't fit your needs I would consider looking into custom solution and slowly build it up over time. Using a web framework, such as Django, can provide a good start to custom solution. It provides a nice administrative interface out of the box to your custom modules. I find it is much easier to develop for and modify than learning the ways and conventions of many of the CMSs available.