Most automatic sentiment is highly dependent on some level of NLP (natural language processing: http://en.wikipedia.org/wiki/Natural_language_processing). Based on what I have seen and heard from folks who are working in that field or using NLP in other areas, it still has a long way to go.

There are plenty of valid reasons why developing accurate NLP systems is not trivial. Take into consideration elements of human language like slang, cultural differences, and context and you can see that there is a lot that has to be tackled before some sense of accuracy can be achieved.

The success of NLP is directly related to how sentiment accuracy evolves on the social web.

Here is a great video I saw some time ago by Jason Falls discussing NLP with CEO of Lexalytics, Jeff Catlin.
There is some interesting tidbits directly related to NLP and what it means for sentiment engines.

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