Sometimes I would poke a bit more in on the side with my finger, rather then pull off and reattach and surprisingly that seemed to work a treat for us.
ME TOO! I also did a whole lot of things "they" said i shouldn't. My BB's are huge so i ALWAYS held the boob i was feeding from steady with my hand. I did pull out my nipple (i also had pain with good attachment and i'm positive it was just the internal anchors of the end of my nipple being stretched out as the pain stopped at a time when they were more consistently "out" rather than flat between feeds) but i was told not to! I squished my nipple down with finger and thumb just back from the areola to make sure as much as possible went as deep as possible into her mouth AND if the attachment wasn't QUITE there but almost and she was really hungry i too would shove a bit more in (used to push mine in underneath against her lower lip).

I'm a big believer that if a mum is well-informed about what she's TRYING to achieve (nipple high in the mouth and way back, near the soft palette) then however she wants to try to do it is all good. The "rules" and advice CAN be really useful, but as we see in so other areas of parenting, if a woman is allowed to get to know her baby in peace and the two of them can figure it out together (especially when there's an LC in the wings to help if need be) they will usually find success together.