can anyone point me towards a/any texts, commentaries, books, pdf's, etc. that help one's understanding of emptiness as it relates to Vajrayana practice specifically?
I have studied some Madhyamika (Chandrakirti, a little Nagarjuna, and so-forth), but I was hoping for something a little more geared towards the Vajrayana practitioner. I study in a terma tradition, if this helps any.
The difference is, emptiness nature in a book is a fancy concept.
The experience of emptiness nature and the means how to get there are a different pair of boots. It's like a map and guidbook of South Africa and actually being there or taking the plane.
You might have a look at the heart sutra and acquaint yourself a little with the basic principles of vajrayana and how it works. Because that explains your question. I also suggest you consult your teacher on the matter. But no intellectual explanation will ever be able to replace a personal experience. Once you had that, even a little glimpse of it, then you can understand how all those teachings all make perfect sense.