The ChurchInsight system must become the primary contact database.
It's important that your staff stop using out of date databases and mailing lists (by deleting them if necessary!), otherwise church members will think changing their web site profile is pointless. Staff and the leadership need to lead the way with using the web site.
Sending emails with attachments will need to be sent from your mail client (mailing from the web site doesn't allow attachments) so you will need to export the Address Book and import into Outlook. To export your address book and receive instructions on importing go to the Address Book on the web site and select Advanced options and then choose format: export to file.
Your web site address book must always be the primary source updated though, as this is the most up-to-date database because members can update their own profiles.