There is no guarantee all reasons for rejection will be listed in your initial rejection response although like the previous poster I have had multiple reasons listed in the "App Submission Feedback" email which tells you of the rejection. But the rejection points were related. If one point for rejection was a HIG violation and another was around In App Purchase I wouldn't be so sure both would be included.
We have also experienced multiple/sequential rejections as we tried to submit the same target version to the store and we've learned a little bit more with each submission.
We have also tried to open up a conversation and get more detail and ask for guidance on how we may have interpreted something differently when we saw some ambiguity. This process is slow and every time we have re-submitted according to the original guideline. Don't pursue this option thinking you might change the policy or get a special exception especially if there is any kind of time sensitivity to your release. I say this especially in relation to this question because even if you were approved for that one item there is no guarantee something else would not be found on your re-submission.
Just as another point of context, most of our rejections have come around In Application Purchase and specific interpretations of the product types.