I've struggled with the same thing - worrying that if I don't intervene right away she may wake too much and this will mean more work than if I just rush in - but we gotta think long term, right, and we don't want to be rushing in for months and months, but instead teach them to resettle.
I am tyring to think of it this way - if my baby is going to wake ANYWAY why not give him a chance and see whether he can do it on his own, and if not, then provide a little help and reassurance as he learns this new skill.