Hi there
I am a very reputed freelancer bidding here in our site freelancer com.
While I do not know about WIN automation, I am sure my programming skills will enable me to come to the solution for the loop you are trying to do. I have automated solutions using Selenium (on python and .net) and on HTMLAgilitypack .NET) so I bet this will build up for taking hands on your project.
No issue working remotely with Teamviewer, I have a licensed version.
Please get in touch for further discuss details
Many thanks
Sergio