Question about the 5 free GMAT score reports

No, you will have to resubmit the scores to the schools you want to get your second score.

In your scenario (send scores to another set of 5), your first 5 schools will only have access to your first score/essays and the second set of schools will have access to both scores/essays.

This is both good and bad. It is good because if you score less the first 5 schools won't see your second set of scores. (This is more of a psychological good than anything else since the schools use only the highest score but applicants are still concerned if their second score is lower). The bad part of course is that you have to resend the scores and potentially pay more. However, for most 5 score reports should be sufficient.

P.S. I have no idea why it is so expensive to send additional score reports. I understand when it was back in the day when you had to physically mail reports but now.... with electronic transfer - not sure.