Thanks for writing this ... I just gave it a whirl....

I have Outlook set to "file as" Last Name, First Name this appears to make the "TO" address in Word come out as:

Smith, Tom
123 Anystreet
Dullville, NC 12345

Is there a way to tell Word to "flip" it?
In the "Full Name" field of Outlook the name is displayed as "Tom Smith"

I have two printers, the other thing I ran into is that it would be helpful to be able to print the envelopes to the non-defaulted printer. I don't see anything right off that would let me indicate that (I've been adding the envelopes to the document and then printing them ....)

Thanks for any pointers if you have time!