Very helpful - thanks for confirming, macropod!

I have been able to test this successfully. I realized that if I copy & paste text from elsewhere in my .DOC, into the field code, it doesn't always show up. (This happens even if I choose to update fields, and save the file.) I am successful when I manually type in the text of War & Peace haha.

Other:
- I used 2 single quotes together, vs a double quote, in the TRUE/FALSE statements. Somewhere on the interwebs I read that this makes sure that Word understands the text in between the quote marks. I see you didn't do that...so I will attempt that myself, too.

New Twist:
-Within the TRUE/FALSE text, can I also add a hyperlink? I don't even need it to mask the URL. I have not been able to save a copy of the merged file in PDF format.

Example:
In the TRUE text of an IF statement:

{IF { MERGEFIELD Salesforce.Custom_Field__c } = "" "Lorem commodo magna eros quis urna.¶
Nunc viverra insert imperdiet enim. Fusce est. ‘‘Vivamus a tellus’’.¶
Pellentesque then click this link here { HYPERLINK "http://www.cnn.com" }."}