For hackerish types exploring Buddhism, I think it's useful to be aware of the concept of upaya, which loosely translates as "skilful" or "expedient". Buddhist teachers consciously make use of metaphors, abstractions and practices that aren't necessarily true, but might aid a particular audience in understanding a difficult concept.

As a result, Buddhist teaching is incredibly diverse, because it's being continually adapted to suit a particular audience in a particular cultural context. One might make an analogy with different programming languages - they all represent the same CPU operations and they're all essentially equivalent via the Church-Turing thesis and the Curry-Howard correspondence, but they often use radically different abstractions.

Personally, I was repelled by what I perceived to be Buddhism on my first exposure to it; I only realised much later that what I understood to be Buddhism was simply an explanation of Buddhist thought tailored for a particular demographic of English-speakers, specifically Californian hippies and new-agers. There was simply a severe impedance mismatch between my mindset and the particular teaching approaches I had been exposed to.

If you think that the Dalai Lama dwells on vapid platitudes or that he's a bit of a smug prick, that's fine - so do a lot of practising Buddhists. He represents a small and rather eccentric school of Buddhism, not Buddhism as a whole. You might gel with the teaching of Ajahn Amaro or Thich Nhat Hanh or Sheng Yen or a multitude of others. You might find it useful to take an ecumenical approach, dipping in and out of various schools to see different perspectives on the same topic.

https://en.wikipedia.org/wiki/Upaya