Oooh *that* is a bug that's been evading our grasp for a while now. The fact that it's repeatable for you is fantastic, well not for your gameplay (sorry), but for us to fix it maybe. It's most likely not related to the number of things on your desk, but probably something is breaking in the transition sequence "screen-wipe" before it "reveals" the next day's desk. If you're down to send us your save file, hop in the discord -- there's instructions in the bug-reports channel.