Need solution with strategy and budget (Selenium+Tesseract? OCR + Browser automation)

In your bid, include the basic strategy and budget for a functional solution. Solution needs to be light enough that multiple ordinary users could set up and run it within 5 or 6 clicks max. Need simple desktop app OR script to add to existing web app OR extension OR in app headless browser OR ? that has the following functionality. Basic goal: for a teacher to transfer column data from one grade book web application to another WITHOUT using a direct API (Using optical character recognition and browser automation). Basically an elaborate copy and paste program for table data. Function: User opens one web page (the source page) and selects column data and the ID row (a column of names) User opens another page (the destination page) and selects a column of input fields and the ID row (contains at least some of the same names as source page) Program identifies the first input cell in the column on the destination page. It then searches horizontally from the selected input cell to see if it finds a name in the ID column that matches one of the names (in ID column) from the source page. If it does, it inputs the correct value for that name into the input cell. The program repeats this process for each cell in the destination column.