The problem is simple: given 2 independent uniform random variables $X, Y$ over $[a, b]$, find $\mathbb{E}[X - Y \ | \ X > Y]$.
My intuitive approach is to first fix $Y = y$, then for this specific case, we have $$\mathbb{E}[X - y \ | \ X > y] = \mathbb{E}[X - y \ | \ X \in [y, b]] = \dfrac{b+y}{2} -y = \dfrac{b-y}{2}$$
Now we can integrate over $Y = y \in [a, b]$ to get: $$ \begin{align} \mathbb{E}[X - Y \ | \ X > Y] &=\int_a^b \mathbb{E}[X - y \ | \ X \in [y, b]] \cdot \dfrac{1}{b-a} \ \mathrm{d}y \\ &= \int_a^b \dfrac{b-y}{2} \cdot \dfrac{1}{b-a} \ \mathrm{d}y \\ &= \dfrac{b-a}{4} \end{align} $$ which is wrong, as the correct answer (verified computationally) should be $\dfrac{b-a}{\color{red}3}$.
What is the flaw in my logic?
You are trying to claim that $\mathsf E(X-Y\mid X>Y)=\mathsf E(\mathsf E(X-y\mid X>y)_{y:=Y})$ but
$$\begin{align}\mathsf E(\mathsf E(X-y\mid X>y)_{y:=Y})&=\int_a^bf_Y(y)\dfrac{\int_y^b~(x-y)~f_{X}(x)~\mathrm d x}{\mathsf P(X>y)}~\mathrm d y\tag{RHS}\\&=\int_a^b \dfrac{1}{b-a}\int_y^b\dfrac{(x-y)}{(b-y)}\mathrm d x\mathrm d y\\&=\int_a^b\dfrac{b-y}{2(b-a)}\mathrm d y\\&=\dfrac{b-a}{4}\end{align}$$
Where as:
$$\begin{align}\mathsf E(X-Y\mid X>Y) &=\dfrac{\int_a^b\int_y^b (x-y)~f_{X}(x) f_Y(y)~\mathrm d x~\mathrm d y}{\mathsf P(X>Y)}\tag{LHS}\\&=\dfrac{1}{2}\int_a^b\int_y^b\dfrac{(x-y)}{(b-a)^2}~\mathrm d x~\mathrm d y\\&=\int_a^b \dfrac{(b-y)^2}{2(b-a)^2}~\mathrm dy\\&=\dfrac{b-a}{3}\end{align}$$