That is promising! Maybe add a column for this.file.day then? (Yes it’ll show the same thing for every row, but the practice of just sticking all the different things in columns works for me because then I know I’m getting dataview’s interpretation of all the stuff at the same time while I’m investigating.) You could also add a column for date(reachout) <= this.file.day AS "Reachout Before Today" (or some other name of your choosing…) and see what appears there!
Below may be just “fun facts” since this doesn’t seem to be your issue, but for clarity:
Then you can simplify the bit before the AND to just WHERE reachout, which will check whether reachout is present or not.
Contains is for checking whether a string or a list (in your case the value of the reachout field) has some thing in it. I suppose a non-existing field does not contain “” and an existing field does, so it works, but I was very confused when I looked at it!