Hi READ,
You haven't disclose much details here but considering the outlines it'll be pretty straightforward to implement. I think python is a good candidate to implement this. So if in future you want to move your system to a server or something it'll run exactly as it's on Windows.
I'll work on the site and pinpoint the requests to generated to simulate it with python. Though if it's heavy on javascript and finding out the requests doesn't worth the effort I can utilize Selenium to handle that as well.
I expect this to be ready to deliver within 5 days at most, probably earlier but it depends on your actual requirements, the details. If this is a rush project I can do better than that but that'll cost extra. We can further discuss your needs, just drop me a message.
Thanks
Aydin