This may be too basic and am just missing a big fundamental block in probability. Suppose there are 4 people in a family. Each one gets picked randomly everyday for doing dishes. Let's say one of them is Bill.
Observer 1:
He starts predicting from day one. Let B=1 be Bill getting picked up and 0 otherwise.
Day 1:
$p(B_1=0) = \dfrac{3}{4}$
Day 2 (and day 1):
$p(B_2=0, B_1=0) = \dfrac{3}{4}\dfrac{3}{4}$
Day n (and earlier days):
$p(B_n=0, B_{n-1}=0, \cdots ,B_1=0) = \Big(\dfrac{3}{4}\Big)^n \tag{1}$
Observer 2:
He just pops up on nth day and predicts the event. According to him then,
$p(B_1=0) = \Big(\dfrac{3}{4}\Big) \tag{2}$
where, for observer 2 its the first day, which was nth day for observer 1. The events are random every day. They are neither in any way depend on observer 1 or 2 , or to one another (that is, event happening on day k is independent of day (k-1)).
So both observers are right in their own way. Then, what is the correct probability for that day, for Bill not getting picked up? Or which is better and why?
It seems like the observers are actually answering a slightly different question than what you stated $B$ to be. For any given day, the probability that Bill isn't picked is always $\frac{3}{4}$. Observations of previous days do not matter.
It seems like the observers are answering this question: "Wow, Bill hasn't had to do the dishes at all! What is the probability of that happening?"
It makes perfect sense that the observers conclude different things. This is because they have different knowledge about what has happened. Let me try to make an analogy.
Let's say there is a geyser that very rarely erupts. On day, I see it erupt - a rare event. A minute later, my friend joins me and sees it erupt again - back to back eruptions are even more rare. My friend says "wow, that was a rare event we witnessed" and I say, "actually, it's rarer than you know!". There is difference because what we are referring to by "this event" are different. My friend is referring only to the eruption he saw, but I am referring to both eruptions.
In your example, Observer 1 has witness more things happening, so he concludes that the situation is more rare than Observer 2. To avoided this error, be careful about what exactly $B$ refers to. Try defining $B_i$ to be the probability that Bill is picked on day $i$ (and day $i$ only).