Can contemplation of the four noble truths lead to penetration of them? Like can  you gain insight into the four  noble truths by contemplating them? In this sutta the Buddha says that "your duty is the contemplation"  and then goes into the four noble truths http://www.accesstoinsight.org/tipitaka/sn/sn56/sn56.048.than.html.
Contemplate here doesn't mean thinking about it intellectually. Sure we all have to think about it first but real insight happens when you realise it through direct experience.You have to experience the four noble truth not churn it through your head back and forth trying to get a sense of it.This is like contemplating how a mango tastes a hundred times Instead of just picking up the fruit and tasting it.