joriki has already presented a solution to Questions 1 and 2; but maybe the following alternate solution has some insight to provide. I'll describe some $n$-tuples of random variables, as sets of vectors in $\mathbb R^n$, with the vectors selected uniformly from that set. For example, with $n=3$, the three random variables $X_1,X_2,X_3$ could be given by the set of vectors $\{(0,1,2), (1,2,0), (2,0,1)\}$ (as in Michael Hardy's comment). Then each $X_i$ individually would be uniformly chosen from $\{0,1,2\}$, but the $X_i$ are far from independent. Notationally, let $e_j = \{0,\dots,0 ,1,0,\dots,0\}$ denote the $j$th standard basis vector in $\mathbb R^n$. Let $f=(1,2,\dots,n)$ and $b=(n,n-1,\dots,1)$.
To begin, consider the following set $U_n = \{u_{ij}\colon 1\le i,j \le n,\, i\ne j\}$ of $n(n-1)$ vectors in $\mathbb R^n$, indexed by ordered pairs of distinct integers from $1$ to $n$, where:
$$
u_{ij} = ne_i + ne_j + \begin{cases}
f, &\text{if } i<j, \\ b, &\text{if } i>j.
\end{cases}
$$
For example, with $n=7$, $u_{52} = (0,0,0,0,7,0,0) + (0,7,0,0,0,0,0) + (7,6,5,4,3,2,1) = (7,13,5,4,10,2,1)$, while $u_{25} = (1,8,3,4,11,6,7)$. Note that for each unordered pair ${i,j}$, there are exactly 2 elements of $U_n$, namely $u_{ij}$ and $u_{ji}$, for which the $i$th and $j$th coordinates are the two largest (each one gets to be largest once). Note also that if $i<j$, then the sign of the $i$th coordinate of $u_{kl}$ minus the $j$th coordinate of $u_{kl}$ always equals the sign of $k-l$; in other words, the random variables $X_1,\dots,X_n$ defined by the set $U_n$ have the property that $\mathbb P(X_i>X_j) = \frac12$ for all $i,j$.
Now we modify the set $U_n$ to account for a given directed graph $G$. Let $V_n = \{v_{ij}\colon 1\le i,j \le n,\, i\ne j\}$, where
$$
v_{ij} = \begin{cases}
u_{ij}+ne_i, &\text{if there's a directed edge from $i$ to $j$ in $G$,} \\
u_{ij}+ne_j, &\text{if there's a directed edge from $j$ to $i$ in $G$,} \\
u_{ij}, &\text{otherwise.}
\end{cases}
$$
For example, with $n=7$, suppose that there is a directed edge from 5 to 2 in $G$. Then $v_{52} = (7,13,5,4,17,2,1)$, while $v_{25} = (1,8,3,4,18,6,7)$. With this modification, it's easy to see (after grokking the notation) that
$$
\mathbb P(X_i>X_j) = \begin{cases}
\frac12+\frac1{n(n-1)}, &\text{if there's a directed edge from $i$ to $j$ in $G$,} \\
\frac12-\frac1{n(n-1)}, &\text{if there's a directed edge from $j$ to $i$ in $G$,} \\
\frac12, &\text{otherwise.}
\end{cases}
$$