I just found out how to do it using WinFax. For some brain-dead reason, I wasn't looking under mail merge. Based off of the following, it looks like I can send WinFax a single document using the following codes to separate faxes:
<<wfxFaxNum>> fax number (maximum 47 characters) <<wfxRecipient>> recipient name (maximum 31 characters) <<wfxTime>> transmit time (HH:MM:SS time format) <<wfxDate>> transmit date (MM/DD/YY date format) <<wfxCompany>> company name (maximum 42 characters) <<wfxSubject>> subject (maximum 79 characters) <<wfxKeyword>> keywords (maximum 33 characters) <<wfxBillCode>> billing code (maximum 26 characters) ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~| Purchase Captivate from House of Fusion, a Macromedia Authorized Affiliate and support the CF community. http://www.houseoffusion.com/banners/view.cfm?bannerid=52 Message: http://www.houseoffusion.com/lists.cfm/link=i:4:190158 Archives: http://www.houseoffusion.com/cf_lists/threads.cfm/4 Subscription: http://www.houseoffusion.com/lists.cfm/link=s:4 Unsubscribe: http://www.houseoffusion.com/cf_lists/unsubscribe.cfm?user=89.70.4 Donations & Support: http://www.houseoffusion.com/tiny.cfm/54