I found a case where it works and a case where it doesn't.
X <- matrix(rep((1:9/9),3), 3,3)
X
[,1] [,2] [,3]
[1,] 0.1111111 0.4444444 0.7777778
[2,] 0.2222222 0.5555556 0.8888889
[3,] 0.3333333 0.6666667 1.0000000
mean(colSums(log(X)))
[1] -2.324398
sum(colMeans(log(X)))
[1] -2.324398
Here is my attempt to show mathematically. I am going to assume n is the length of each sample X in this case.
\begin{align}
E\bigg(\sum^n_1 \log(X_i)\bigg) &= \frac{\sum^n_1 \log(X_1) + \sum^n_1 \log(X_2) + ... \sum^n_1 \log(X_n)}{n} \\[10pt]
\sum^n_1 E\big(\log(X_i)\big) &= \sum^n_1 \frac{\sum^n_1 \log(X_1)}{n} + \frac{\sum^n_1 \log(X_2)}{n} + ... \frac{\sum^n_1 \log(X_n)}{n} \\[10pt]
&= \frac{\sum^n_1 \log(X_1) + \sum^n_1 \log(X_2) + ... \sum^n_1 \log(X_n)}{n}
\end{align}
If the size of $X$ is different they would not be equal.
> X <- matrix(rep((1:12/12),4), 4,3)
> X
[,1] [,2] [,3]
[1,] 0.08333333 0.4166667 0.7500000
[2,] 0.16666667 0.5000000 0.8333333
[3,] 0.25000000 0.5833333 0.9166667
[4,] 0.33333333 0.6666667 1.0000000
> sum(colMeans(log(X)))
[1] -2.457916
> mean(colSums(log(X)))
[1] -3.277222
\begin{align}
\sum^n_1 E(\log(X_i)) &= \sum^n_1 \frac{\sum^n_1 \log(X_1)}{k} + \frac{\sum^n_1 \log(X_2)}{k} + ... \frac{\sum^n_1 \log(X_n)}{k} \\[10pt]
&= \frac{\sum^n_1 \log(X_1) + \sum^n_1 \log(X_2) + ... \sum^n_1 \log(X_n)}{k}
\end{align}
where $k$ is the length of each $X$ and $k \ne n$.