Hello,
I have several years of working experience as a Test automation engineer. My expertise includes automation framework development for Web based application, windows application and andorid,iOS application. Your bot requires automation skill in both web application and windows application. In order to solve your problem I will use the tool called Sikuli, Selnium and Python programming language. I will make automation script very simple so that you can use this efficiently. It will take less than 3 days to complete the task. Could you please tell me details about your website and windows version you gonna use for installation.