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Pareto
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Henry
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Since it came up in comments, here is an equivalent simulation for a heavy-tailed Pareto distribution with $\alpha = 1.5$ (so initially an expectation of $3$ but infinite variance, so optimistically relying on LLN convergence of the sample mean); the initial drop due to the heavy tail is much faster with a simulated mean of $2.99875$ to start and $2.91492$ after one removal. If a single sampled value is extremely high, then it is very likely to be removed in the first step due to its high weight.

X <- runif(N)^(-1/1.5) # distribution must take positive values

Pareto

Since it came up in comments, here is an equivalent simulation for a heavy-tailed Pareto distribution with $\alpha = 1.5$ (so initially an expectation of $3$ but infinite variance, so optimistically relying on LLN convergence of the sample mean); the initial drop due to the heavy tail is much faster with a simulated mean of $2.99875$ to start and $2.91492$ after one removal. If a single sampled value is extremely high, then it is very likely to be removed in the first step due to its high weight.

X <- runif(N)^(-1/1.5) # distribution must take positive values

Pareto

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Henry
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I doubt this is an easy analysis, as the result is going to be affected by the distribution used for $P(k)$. I doubt there is a general form, but empirically there may be a well-behaved example.

In any case, it seems possible to simulate what happens. There is no need to require the $P(k)$ to be integers so long as there probability $1$ that all the samples are positive.

For example, if $P(k)$ has an exponential distribution with rate $\lambda$ i.e. mean $\frac1\lambda$, it seems from simulation that the expectation of the remaining empirical mean might be $\frac{N-n}{N}\frac1\lambda$ or close to that. As an illustration, here is a simulation using R, with $\lambda=\frac15$ and $N=10^3$ and averaging over $10^4$ cases:

set.seed(2024)
N <- 10^3
numbersims <- 10^4
remainingmean <- function(N){
  X <- rexp(N, 1/5) # distribution must take positive values
  Y <- sample(X, size=N, replace=FALSE, prob=X)
  return((sum(Y) - c(0,cumsum(Y)[-N])) / (N:1))
  }
sims <- replicate(numbersims, remainingmean(N))
plot(0:(N-1), rowMeans(sims), xlab="n removed", ylab="remaining mean") 

exponential

There is a distribution on the positive integers $\{1,2,3,\ldots\}$ similar to an exponential distribution, namely a suitable geometric distribution, and replacing the appropriate line in the code above with

X <- rgeom(N, 1/5) + 1 # distribution must take positive values

seems to produce a broadly similar chart (though necessarily heading towards $1$ rather than $0$):

geometric

while a distribution with a lighter tail and a smaller variance, say a Poisson distribution plus $1$, declines more slowly initially

X <- rpois(N, 4) + 1 # distribution must take positive values

Poisson

while a distribution with a heavier tail and greater variance, say the square of the geometric distribution, declines more quickly initially.

X <- (rgeom(N,1/5) + 1)^2 # distribution must take positive values

square of geometric

Apart from the unforeseen apparent linearity with an exponential distribution, this all seems intuitively reasonable, at least comparing one distribution with another. But it is not quite as simple as that: adding $1$ to the exponential distribution (so not changing the shape of the tail or the initial variance) keeps the close to linearity effect initially, but visually slightly deviates from it as $n$ reaches $N$ and so presumably deviates initially too but to a lesser effect.

X <- rexp(N, 1/5) + 1 # distribution must take positive values

exponential plus 1