I wrote, self-published, and marketed a book on dyslexia a few years ago that received several favorable reviews and sold over six thousand copies in a dozen countries. I have recently decided to make this book available for free public distribution and have already made copies available on Facebook. I am now in the process of copying lists of email addresses from online directories for school faculty and staff to whom I plan to send free copies of my book via email as attached pdf files. I am working on this project in my spare time and should have a list compiled that consists of thousands of email addresses in a few months. These lists will be blocks of email addresses for different schools which each use separate internet servers.
I have recently become aware that these emails will likely be received as Spam by Internet servers if I send one email to twenty or thirty email addresses for one school at a time. In order to resolve this problem, I need to know if there exists software that will rearrange the order of email addresses on a list like shuffling a deck of cards. I understand that these emails will pass through Spam filters if each email is sent to email addresses for several schools at a time.