From what you say he seems very knowledgeable, you are fortunate to have access to a real life experienced teacher.
I believe I mentioned this previously, about 5 years ago I hit my bottom.
I was abusing alchohol, addicted to cigarettes, prone to violence, pretty much one of the most miserable humans in existence. A moment of awakening occured, I got to take a look at what I had become in a very unique way. Alchoholics call this a moment of clarity(and it truly is just that). This moment of clarity gave some sort of wisdom to me which allowed me to walk away from alchohol and ciggarettes instantly I've never had a desire to return to them. This also gave me some sort of fuel to start down this path although I did not know this path existed.
My wife gave me a book written by Eckhart Tolle (a new earth) and it radiated with me at my core, it wasn't long after that that I found myself at the door of my local buddhist temple where I met the Bhante who has helped me so much. Through this centre I have found many dhamma brothers and sisters and one introduced me to the Goenka vipassana centre which I am fortunate to have one hours drive from my home. There I have found many teachers and friends in the dhamma and my technique for practicing the dhamma. Having questions that I needed answers to but were afraid to ask in person or simply lacked the words, I found this forum where I have met all of you, more dhamma brothers and sisters.
I am convinced that when one starts down the path of dhamma we come in contact with a higher power that sheppards us along the journey, I certainly feel truly fortunate for these blessings, and also for my supportive family.
The dark night!!!!
I believe I was one of those dry insight workers you mentioned, purification through pain has been my experience. I've had retreats where sitting felt like I had battery acid pumping through my veins. My first day at Goenka retreat, ( I had sat a couple other retreats at the temple prior) and I was ready to quit, I literally did not think I could survive the pain. I remember finishing the day at 9 pm and limping my way back to my room. I thought I had done permanent damage to my legs, back, shoulders, head, ankles, feet, butt etc.... I crawled into bed seriously frightened of the next day, but to my amazement I woke completely soaked from sweat but with absolute clarity the pain was gone and I had this new mind to meditate with, I got to the meditation hall and sat for the first time for an hour and a half with no pain and the time went by fast, it was then that I realised that my state of mind was causing my suffering.
It has not been smooth sailing since then but this insight and a few others have allowed me to strengthen in equiminity. The first day at goenka retreat seemed to be my single darkest night, nothing has been as difficult as this first night. Some dealings with anxiety have been tough but managable. Perhaps the fact that my entire life up to my awakening was a dark night I was cut some slack. Or maybe the real heavy self had fallen away somewhat with that moment of clarity, I don't know but I know that life is a heck of alot easier now.
The darknight can't exist when we shine the light of awareness on it. But it helps to have the biggest bloody light you can!!