For interest sake, and to address the question of how one might calculate the expectations, and perhaps as motivation for why this is avoided in the general case, I provide a direct proof for a specific case, where the first $n-1$ vertices have the same degree $d$ and vertex $n$ has degree $d'\neq d$.
Denote by $F_i$ the largest subset of $[n]$ such that there is an edge from vertex $i$ to every element in $F_i$ (so $F_i$ is the neighbourhood of $i$). Then
$\mathbb{E}[X_n] = \frac{(n-1)d + d'}{n}$
And
$ \mathbb{E}[Y_n] = \frac{1}{n} \sum_{i\in [n]}\sum_{j\in F_i}\frac{d_j}{d_i} $
In this specific case we can simplify the expression for $\mathbb{E}[Y_n]$
$\mathbb{E}[Y_n] = \frac{1}{n} \left(\sum_{i\in [n-1]} \sum_{j \in F_i}\frac{d_j}{d_i} + \sum_{j\in F_n}\frac{d_j}{d'}\right)$
$ = \frac{1}{n} \left(\sum_{i\in [n-1]} \sum_{j \in F_i}\frac{d_j}{d_i} + \sum_{j\in F_n}\frac{d}{d'}\right)$
$ = \frac{1}{n} \left(\sum_{i\in [n-1]} \sum_{j \in F_i}\frac{d_j}{d_i} +\frac{d\cdot d'}{d'}\right)$
Since all of the vertices in the neighborhood of vertex $n$ have degree $d$, and there are exactly $d'$ of them. Now to compute the left hand sum, note that exactly $d'$ of the vertices in $[n-1]$ have vertex $n$ i
their neighbour, for these vertices the average degree in their neighbourhood is $\frac{(d-1)d + d'}{d}$ and for the remaining $n-d'-1$ vertices, their average neighbourhood degree is just $d$. So the left hand sum gets replaced with these expressions and we get
$ = \frac{1}{n}\left(d'\cdot\frac{(d-1)d + d'}{d}+ (n-d'-1)d +d\right)$
Comparing this to the expression for $\mathbb{E}[X_n]$ we see they both share a common factor $\frac{1}{n}$ Which we can get rid of for the comparison, as well as a common term $n\cdot d$. We are then left comparing
$$ -d+d' $$ with $$ -d'\cdot d + \frac{d'(d-1)d + d'^2}{d} $$
The second expression simplifies a bit to
$ - d' + \frac{d'^2}{d} $
So according to the theorem, we should get
$$ -d + d' \leq - d' + \frac{d'^2}{d} $$
Or $$ 2d'd \leq d^2 + d'^2 $$
Or $$ 0 \leq (d-d')^2 $$
Which is indeed true for any natural numbers $d$ and $d'$ . And this equality is of course strict when $d=d'$. As you can see however, this argument is probably too complex to generalise, but I think its interesting to see how the algebra works out.