This method for creating a random permutation is used by poker players for estimating their expected value in a tournament which pays prizes for places lower than first. It is called the Independent Chip Model or ICM. The probabilities don't simplify that much although you can do better than the naive summation. I'll give a few different ways to describe this random permutation.
Choose a winner proportionally. Eliminate that player, and rescale the probabilities, then choose the second place finisher proportionally. Repeat until all places are assigned.
Each player has some integer number of chips in the proportion $p_1 : p_2 : ... :p_k$. Randomly eliminate one chip at a time so that each chip has an equal chance to be removed. When a player's last chip is eliminated, the player is knocked out. Players are ranked in reverse order of being knocked out.
I don't think it is obvious that these generate the same distribution on permutations. The second requires rational ratios between the probabilities, and is it obvious that doubling the number of chips won't change the distribution? However, a third description connects the two.
- Each player has some integer number of chips in the proportion $p_1 : p_2 : ... :p_k$. Shuffle the chips. Sort the players by their highest chips. If you reveal the chips one by one from the bottom, you get the second method. If you reveal the chips from the top, you get the first.
Anyway, there are a few known results about the equities according to the ICM. For example, I proved that if prizes are nonincreasing, then the equity is concave, so players should be risk-averse in heads-up pots. Also, there are some ICM calculators, such as my program ICM Explorer, which you can download and use to calculate the finishing probabilities for up to $10$ players.
I haven't thought much about your particular problem, but I think the second description, eliminating chips to knock players out, may be helpful. I did look at the probabilities of finishing last, or the case of $k=1$, for some particular cases.