If you want to get a handle on Heidegger, I recommend working through Being and Time while listening to Prof Hubert Dreyfus's UC Berkeley lecture series, 'Philosophy 185 - Heidegger'. I heard them on ITunes U long ago, but they are also available on archive.org [0].

Dreyfus wrote a critique of AI, "What Computers Can't Do" in the 70s, and talks a bit about a Heideggerian approach to AI in his lectures which may be of interest to a few people here.

[0] https://archive.org/details/Philosophy_185_Fall_2007_UC_Berk...

He's following the German philsophical tradition of verbosity for its sake. But there is a small kernal of ideas that can be distilled from his work that academics generally agree are there and original enough for the time to be worth consideration. Interpretations vary wildly, of course, but that has almost as much to do with academia as it does Heidegger.