Imagine we have six nodes, labeled 0 through 5. One can transition from node $i$ to $i+1$ with probability $p$ or can remain at node $i$ with probability $1-p$. Note that once one transitions to a node, it cannot backtrack. See the following figure for an illustration.
I want to know the expected time it takes to reach node 5 assuming you start at node 0. I started to write down the following outcomes below:
- 5 transitions, 0 stops (5 time-steps)
- 5 transitions, 1 stop (6 time-steps)
- 5 transitions, 2 stops (7 time-steps)
- and so on...
where "stop" means no transition was made. Once we list all of the cases then it's just a matter of computing the probabilities. Problem is, I don't know how to write out all of the cases (infinitely many?). Is this the right way of thinking about it?

The easier way to approach this problem is to take advantage of linearity of expectation by expressing the transit time as a sum of i.i.d. geometrically-distributed random variables, as in Daniel Xiang’s answer, but it can certainly be attacked the way you propose: by computing the probability that it takes a given number of time steps to reach the end and then finding the sum of the infinite series that directly results from the definition of expectation.
Let $Y$ count the number of time steps to transit the chain. Since every transit takes at least five steps, we’ll focus on the probabilities of extra time being taken—of there being $k$ stops during the transit. Let the random variable $X=Y-5$ count these extra steps. As you’ve already determined, $\Pr(X=k)$ is equal to $p^5(1-p)^k$ times a coefficient that counts the number of ways that the stops can be distributed throughout the transit. This is a typical stars-and-bars problem, from which we can easily work out this coefficient: $$\Pr(X=k)=\binom{4+k}4p^5(1-p)^k$$ so $$E[X]=\sum_{k=0}^\infty k\Pr(X=k)=p^5\sum_{k=0}^\infty k\binom{4+k}4(1-p)^k=p^5{5-5p\over p^6}=5{1-p\over p}$$ and $$E[Y]=5+E[X]=\frac5p.$$