Interesting thoughts!
I guess the fundamental, fast and frequently change of mind states in a consequent meditation practice can sometimes cause the feeling of dissociation. And besides, as you said, seeing phenomena through the "vipassana lense" cuts their relativity to their place in the world. For me, feelings and thoughts in their substance give us directions and movements in life, whereas insights show us the directionlessness (is that a real word?

) of anything. There's definitively a difference between experiencing a feeling in the movement, without control, as reacting subject and just looking at it from an transcendental view point. Speaking about your world is not your world and will in addition even change it. It is said, that when the clinging ends, the suffering will end and I see that as possibility for every human situation. Even the clinging to perceive phenomena vipassan style or somehow spiritual will cause unnecessary suffering. But dharma and experiencing phenomena "in the movement", "in its core" don't have to be contradictory to each other. Quite the contrary, I see progress in practice where you loose clinging to every factor of your experience. Eating a chesseburger and being ashamed about it, sitting and watching the breath, having a blackout while drinking vodka, seeing mind, seeing no mind - no clinging, no problem

The problems you describe remind me a little of Jack Kornfields view that there is a huge step from practicing dharma to really living it.
I hope I did get you right here, English is unfortunately not my (philosophical) mother tongue