(I have also posted this on MO) So I've had this problem in the back of my mind for a while.
I recall having seen a rigorous solution using some advanced probability theory, but I've lost the reference and I must admit the result is intuitively not too obvious to me. The fast way to convince me that the problem is correct is by simulation, so I'd like to gain new perspectives in order to adjust my intuition.
What I'm asking is whether you can provide me with some solution which is (ideally) both rigorous and intuitive. That being said, any light shed on the subject is very much appreciated. Also, in what way can that solution be generalised to a more general setup?
Problem: Consider an iid sequence $(X_n)_{n\in\mathbb{N}}$ corresponding to independent tossing of a fair die. Define $$\tau_{5,6}=\inf\{n\in\mathbb{N}:X_n=5,X_{n+1}=6\}, \:\:\:\tau_{6,6}=\inf\{n\in\mathbb{N}:X_n=6,X_{n+1}=6\}.$$ Then $E\tau_{5,6}<E\tau_{6,6}$.
Extension: Actually $E\tau_{5,6}=36$ while $E\tau_{6,6}=42$.
In the first case you roll the die until you have a five, then if the next die is not a six it might be a five.
$$\mathsf E(\tau_{56}) = \mathsf E(\tau_5)+\mathsf E(\tau_{56}\mid h_5) \\ \mathsf E(\tau_{56}\mid h_5) = \tfrac 16+\tfrac 46\mathsf E(\tau_{56})+\tfrac 16\mathsf E(\tau_{56}\mid h_5)$$
In the second case, you roll the die until you have a six. If the next die is not a six it can't be a six.
$$\mathsf E(\tau_{66}) = \mathsf E(\tau_6)+\mathsf E(\tau_{66}\mid h_6) \\ \mathsf E(\tau_{66}\mid h_6) = \tfrac 16+\tfrac 56\mathsf E(\tau_{66})$$
So the intuition is that in the first case you may have a second chance at getting a six followed by a five if you get a five followed by a five.