Problem: If a six-sided die is fair, what is the expected value of the difference between two die rolls?
Attempted solution: The expected value can be thought of as the midpoint of the outcomes. If the die is rolled twice, the difference of the two sides could be $$0,0,0,0,0,0,1,1,1,1,1,2,2,2,2,3,3,3,4,4,5$$ The midpoint is then $1$. Here, I have assumed that two rolls with sides $4,5$ is the same as $5,4$.
Is there a more sensible way to answer this problem?
There is some ambiguities in your OP regarding the definition of "difference", and we discuss them separately. Let $X$ be the outcome of the first die, $Y$ be the outcome of the second die, and $D$ is the "difference".
Case.(1) If the "difference" includes those negative outcomes, namely $D=X-Y$. (For example, when $X=1, Y=4$, we get $D=-3$.) Under this definition of $D$, we get
$$\boxed{\mathbb E(D)=\mathbb E(X-Y)=\mathbb E(X)-\mathbb E(Y)=3.5-3.5=0}$$
Case.(2) If the "difference" means the absolute distance, namely $D=|X-Y|$, then we have
$$\mathbb E(D)=\mathbb E(|X-Y|)$$
When we compute $\mathbb E(|X-Y|)$, there are three subcases,
(i) if $X=Y$, then $\mathbb E(|X-Y|)=\mathbb E(0)=0$
(ii) if $X>Y$, then $\mathbb E(|X-Y|)=\mathbb E(X-Y)$
(iii) if $X<Y$, then $\mathbb E(|X-Y|)=\mathbb E(Y-X)$
Due to symmetry, case (ii) and (iii) are equal, hence we get
$$\mathbb E(D)=\mathbb E(|X-Y|)=0+2\cdot\mathbb E(X-Y),~~~\text{where}~~X>Y\tag{1}$$
Next, we compute the probability for each outcome,
$$\begin{align}X-Y&=1\Leftrightarrow (X,Y)=(2,1), (3,2), (4,3), (5,4), (6,5)\Leftrightarrow P(X-Y=1)=\frac5{36}\\ \\ X-Y&=2\Leftrightarrow (X,Y)=(3,1), (4,2), (5,3), (6,4)\Leftrightarrow P(X-Y=2)=\frac4{36}\\ \\ X-Y&=3\Leftrightarrow (X,Y)=(4,1), (5,2), (6,3)\Leftrightarrow P(X-Y=3)=\frac3{36}\\ \\ X-Y&=4\Leftrightarrow (X,Y)=(5,1), (6,2)\Leftrightarrow P(X-Y=4)=\frac2{36}\\ \\ X-Y&=5\Leftrightarrow (X,Y)=(6,1)\Leftrightarrow P(X-Y=5)=\frac1{36}\\ \end{align}$$
therefore,
$$\mathbb E(X-Y)=1\cdot\frac5{36}+2\cdot\frac4{36}+\cdots+5\cdot\frac1{36}=\frac{35}{36},~~~\text{where}~~X>Y$$
Finally, use eq.(1), we get
$$\boxed{\mathbb E(D)=2\cdot\frac{35}{36}=\frac{35}{18}}$$