Christmas Card Mail Merge
If you’re willing to make precisely zero edits to the address labels that are created from the Contacts app, it’s actually quite easy to print labels. […] For me, I wanted to address couples as, say, “Stephen and Merri Hackett”, even if my contact card had only Stephen’s name in it. This got very complex very quickly, but I was able to figure it out.
He exports to CSV, edits the file in Numbers, and uploads it to the Avery Web site to get it formatted (I guess as a PDF).
I had thought that Address Book’s (now Contacts’) support for custom fields would eventually solve this problem. Make a field for how you like the name printed and make a group with all the contacts you want to print. Then just keep the addresses up-to-date throughout the year. But, in practice, one ends up making the same manual name changes each year. And there’s no good way to sync contacts between different users. We end up maintaining several parallel address lists in Google Docs and then copying/pasting individual addresses into the DYMO software.
