Sending emails to one Contact with multiple Addresses

Hi,
I am a volunteer with youth sports, and frequently need to send emails to entire teams of kids.  I have the players all listed as one contact, but have the email addresses both parents and themselves listed under their contact.  When I send an email, I need it to go to all listed, Parents and Players.
Separating the contacts would be a disaster, as when I need to contact a player I always need to contact, Mom, Dad, and Player...
I did create a group for my team, thinking this was the solution to my issue.  Unfortunately, when I went to send an email, it only went to one email for each player.   That lead to many complaints "Why did I not get the message"...
Love everything Mac so far, but this is killing me... and may keep me away. Outllook lets me do it so easily, why not mac.
I would appreciate any help.

Thanks - starting a brand new SMS rather than continuing an existing thread gave me the option of which number to choose, and the thread then switched to show all the messages related to that number.

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