Yes, the left-hand side is the probability of the added player winning, and the expression on the right is another way to state that same probability.
Don't think of it as an expectation, think of it as a probability of winning. p(n) is the probability that the score to beat is n. (1-n/106) is the probability of player #5 winning, given n. So sum_n p(n) *(1-n/106) is the full probability that player #5 wins, so =1/5. But when we evaluate the sum, we find it is 1 - N/106, where N is the expectation value of the score to beat. So we get an equation involving N that let's us solve for N.
Correct, but it is the chance of greater than n, and since p(n) is the probability that the score to beat is n, we get our result without ever knowing what p(n) actually is-- which is the work-saving part!