In the process of thinking about this question, I realized that I don't understand something very fundamental about operator product expansions.
Consider a product of 3 local operators in a 2d CFT:
$$ X(x) Y(y) Z(z) = \sum_{n=-N}^{\infty} A_n(x) Z(z) (x-y)^n, $$
where we have substituted $X(x) Y(y)$ for the $XY$ OPE. This expression contains the singular terms for $x = y$.
Now because by definition of OPE $A_n(x)$ is a local operator at $x$, we can use the $A_n Z$ OPE again:
$$ X(x) Y(y) Z(z) = \sum_{n=-N}^{\infty} \sum_{m=-M}^{\infty} B_{nm} (x) (x-y)^n (x-z)^m. $$ This expression contains the singular terms for $x = y$ and $x = z$.
Question: where did the $y = z$ singular terms go?
This is likely related to the convergence of the series, but I wasn't able to formulate a convincing argument.