Distribution List & Other Address Book

Please help to answer 2 impt questions:
1.
I’m asked to create a distribution list of parents with their internet emails. Total 1000 parents in the school for principal to email. How can I go about in creating this list (given .csv file) and to create another address book so that staff will not see/use the DL. We are using Exchange 5.5.

2. I have to upgrade Windows NT 4 to Windows 2000 on the Exchange 5.5 server. This is to prepare for Windows 2000 active directory in months to come. My question, can I just set the Windows 2000 CD on the server to upgrade OS. What is the best solution without affecting the production.

Thanks in advance.