A friend just made the jump from PC to Mac and found that iWork didn’t print envelopes for him easily. He ended up using Word.
I suggested that he check out EasyEnvelopes, which is free Mac OS X dashboard widget. You just activate the widget, type in your friend’s address, select the person from your address book, and print. It could only be easier if the widget loaded your envelope into your printer for you (with the correct orientation). EasyEnvelopes’ biggest limitation is that it’s only designed for printing a single envelope. It’s not a mail merge program.
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