My events only show up in the top half of the day in the monthly view so I can only get two events to show. The arrow points to more messages but it seems like I should be able to fit three events at least.
If you talking about Outlook calendar, it seems like this parameter depends on your window size. Third item shows up when your windows is about 730 pixels high (standard scaling), fourth - 900 pixels high. You can minimize ribbon (little arrow in the top right corner of the window) or change resolution to get more useful space on the screen, but looks like that's about it.
Your suggestion to minimize the ribbon worked great. In fact, I took all folders off of the calendar page so that it allows me four entries every time.
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