You are in the right place for help. A lot of very talented people on the forums every day.
Have you tried using UiExplorer to try and find these elements of ‘grey’, ‘white’ and ‘both’.
Take a look at this tutorial on UiExplorer.
Once you have found your selector and Attribute Take a look the ‘Get Attribute’ activity.
Check these Links to learn about the Get Attribute Activity:
I haven’t done anything too similar to your project but you could try and map every day for the entire month in a DataTable with its “status” (Column1) then insert what is requested into Column2 (call “Requested”). Then compare Column1 + Column2 and store that result in a third column (“Result”). Then check “Result” for any False/Fails. This might be a suitable option?