Help needed automate multiple faxes to multiple recipients

Here is what I do each month in my business of buying and selling houses
1. I down load a list of houses for sale from a mls realtor database to excel.
2. The ones I want to bid on I copy to a separate file which I use as the data source for datamerge with word (about 50).
3. Create and save the 50 unique contract offers in one big word doc from the data merge
4. Separate and save each contract offer via a word macro sequentially to get 50 files
5. Applescript renames each file by matching file name to a field on the excel table, which is the fax number.
6. Applescript drops each of those faxes into one folder called 'septoffers'
Requirement 1: I need to be able to take each of those files from the folder and fax them to the desired recipient, whose fax number is now the filename (can also use the excel file that was used to match files to fax number). I'm using Pagesender, but am open to other fax apps
Requirement 2 The goal is also to automatically send the same fax weekly, which conditions the recipient to know that I am interested in their house and keeps us engaged until I can get them to accept my low offer.
If I had to use scanner, it would take all day and I would quickly quit doing it. Doing this from the print to fax in os x would take all day, as would using a scanner.
Please If you can help me with a script or workflow I would really appreciate it.

I've seen this, but sorry, no ideas other than bringing it to the top again.

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