If everyday is like a coin flip (totally independent of the previous flip and previous day), then statistically speaking the odds are the same every day. If you know he trespasses 1 day every month, then the odds would increase as each day passes.
I remember arguing with my college statistics teacher about the coin flip until we both got tired. LOL. I understand the odds stay 50% on every flip, but I also understand that in theory 1 out of 2 should equal close to 500 out of 1000. So if it lands heads 40 times in a row, it has to catch up sooner or later - statistically speaking