This didn't go right the first time, so I'm going to drastically rephrase the query.
As per this previous question, I am wondering if the two series $$\frac{f(a)+f(b)}{2}\frac{(b-a)}{1!}+\frac{f'(a)-f'(b)}{2}\frac{(b-a)^2}{2!}+\frac{f''(a)+f''(b)}{2}\frac{(b-a)^3}{3!}+\cdots$$
and $$\frac{f(a)+f(b)}{2}\frac{(b-a)}{1!}+\frac{f'(a)-f'(b)}{2^2}\frac{(b-a)^2}{2!}+\frac{f''(a)+f''(b)}{2^3}\frac{(b-a)^3}{3!}+\cdots$$ could possibly be equal. The only difference is the powers of $2$ in the denominator.
NOTE: the numerator is $f^{(k)}(a)+(-1)^kf^{(k)}(b)$ in general.
The identity you give is quite pretty! Yes they are equal.
Let $$\phi(t) = \sum_{n \ge 0}\frac{(b-a)^{n+1}}{(n+1)!} \left( f^{(n)}(a) \cdot t^{n+1} + f^{(n)}(b) \cdot (-1)^n (1-t)^{n+1}\right).$$ The first series in question is $\frac12(\phi(1)+\phi(0))$ and the second is $\phi(\frac12)$. The "why" is that these are equal because, in fact, $\phi$ is constant: $$\phi(t) = \int_a^bf(x) \, dx$$ for all $0 \le t \le 1$. The proof is by splitting the integral into two as $$\int_a^bf(x) \, dx = \int_a^{a(1-t)+bt}f(x) \, dx + \int_{a(1-t)+bt}^bf(x) \, dx$$ and evaluating the first by expanding $f$ as a power series about $a$ and the second by expanding $f$ as a power series about $b$. You will get $\phi(t)$ as the result.
Specifically, the "when" is the condition that the power series expansions $$f(x) = f(a)+f'(a)(x-a)+\frac{1}{2!}f''(a)(x-a)^2+\cdots$$ and $$f(x) = f(b)+f'(b)(x-b)+\frac{1}{2!}f''(b)(x-b)^2+\cdots$$ are valid for all $x \in [a,b]$.
At the risk of sounding totally banal, I've basically just briefly rehashed (and slightly generalized) the derivation you linked to $-$ that post in itself already gives the proof.