Successfully sending a group email using Outlook

I have just spent hours trying to send a group email using the dreaded OUTLOOK ( formerly known as hotmail)  and each time I get a different message ranging from : do not use nicknames; do not use abbreviations and the list goes on. As a matter of fact it got to the point where almost all of my "N" contacts  were deleted. Yet using the SAME addresses for an individual email works just fine! I am terrified that after all of the work of putting the list together I will a) lose the whole list or worse yet not be able to use this supposed feature! Very very frustrating. I have called the recommended numbers to speak to someone about this and have yet to recieve help solving the issue. I am very upset!