Automation - Outlook

Would any of the Outlook gurus have a solution to my need.

Task :
A folder has several hundred files to be emailed to several hundred recipients.  

Information :
The files include the recipient name in the filename. (i.e. C:\users\userone\documents\jones-h.docx)
The recipients are listed in the contacts in Outlook.
If there was a way to stagger the sending it would be handy (i.e. send say 50 today, 50 tomorrow....)
Keep track of what has been sent say in a text file
Email Client is OLK 2013 running on Windows 10
OLK is using IMAP

I see malware doing this quite easily :) but I don't think I'd like to hunt one down for this task
Who is Participating?
Vba scripting is likely your best bet that goes through the word docs, extracting the data and ..

Logic seems, potentially the sent items will be included in the outlook's sent items...

The issue is how the entry in the address book relate to the name of the file.
Testing first that you can list the address book and match the correct recipient.
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