Import transactions from CSV statements into Quicken, no matter how many years back they go.And the.vcf files don't include all info in Outlook contacts. It's a slow & boring chore, but perhaps that's the only way to do this. By the System Contacts app, do you mean the Apple address book that is in the dock as Contacts? I've dragged.vcf files there in the past, but I have 9,000+ contacts, and that app seems to only allow 2,000 or so to be added at a time. I've previously dragged all contacts as v-cards/.vcf files to a folder on the desktop.