I think intuition is tough here. Is it obvious that it should take longer to see $55$ than to see $56$? Well, at least that can be made intuitive:
Conway's Algorithm is very useful here.
The idea is to track the places where the desired string restarts. For $56$, there is no restart. For $55$, it starts twice (so to speak). For $563563563$ it starts $3$ times These place represent the various points at which partial successes might overlap.
The idea is that it takes longer to see a string that repeats the first entry. Why? Well, consider $56$ versus $55$. If you are trying to see the latter then, having just tossed a single $5$, your only hope is to toss another immediately, else you start at the beginning. With $56$ then, having thrown a $5$, you have two possibilities for a favorable next throw. Either you throw the $6$ and win, or you throw another $5$ and remain in the active state.
Conway directs us to compute expected sample sizes accordingly. $56$ has expected sample size $6^2$, as you have found. $66$ has expected sample size $6^2+6=42$. and $563563563$ would be $4^9+4^6+4^3$
This quick algorithm can be demonstrated using the Markov methods described in the post you link to.
Not sure I'd call this "intuitive" but it does give a very fast way to compute the desired expectation. I wouldn't want to work that out for $563563563$ by solving a $9\times 9$ linear system.