Your definitions of the two conditions numbers seem to be inconsistent with each other. A slight sticking point is that different authors define the Jacobian differently. Some use (A) $J_{ij} = \partial f_i / \partial x_j$ and others use (B) $J_{ij} = \partial f_j / \partial x_i$. With the first definition, we have that $f(x+\Delta x) = f(x) + J(x) \Delta x + O(\|\Delta x\|^2)$ and with the second we get $f(x+\Delta x) = f(x) + J^\top(x) \Delta x + O(\|\Delta x\|^2)$. The first definition appears to use the definition (A) of the Jacobian and the second definition definitely requires one to use definition (B) for the product $|J^\top(x)||x|$ to be well-defined. In the case that the norm $\|\cdot\|$ is transpose-invariant $\|A\| = \|A^\top\|$ it doesn't matter which definition you use. There are enough notational consistencies between different authors that it's hard for me to exactly disambiguate what's happening here. I checked popular numerical linear algebra books (Golub and Van Loan, Trefethen and Bau, Demmel, Higham) and could not find any other explicitly using this particular set of definitions. Perhaps if you could find another source with this set of definitions, I (or someone else) could help further.
Let me now address your main question. Suppose I want to solve the diagonal system of linear equations
\begin{equation}
\underbrace{\begin{bmatrix} a & 0 \\ 0 & b \end{bmatrix}}_{=A} \begin{bmatrix} x \\ y \end{bmatrix} = \begin{bmatrix} 1 \\ 1 \end{bmatrix}.
\end{equation}
This corresponds to the function $f(a,b) = (a^{-1},b^{-1})$ with Jacobian
$$
J(a,b) = -\begin{bmatrix} a^{-2} & 0 \\ 0 & b^{-2} \end{bmatrix}
$$
which has norm $\|J(a,b)\| = \max(a^{-2},b^{-2})$ in the operator $\infty$-norm. Let's assume going forward that $a > b > 0$ so $\|J(a,b)\| = b^{-2}$. The first condition number is then
$$
\kappa_1(f(a,b);(a,b)) = \frac{\|J(a,b)\|}{\|f(a,b)\|/\|(a,b)\|} = \frac{b^{-2}}{b^{-1}/ a} = \frac{a}{b}.
$$
Thus if $a\gg b$, this problem is very ill-conditioned. Now, let's look at the component-wise condition number
$$
\kappa_2(f(a,b);(a,b)) = \frac{\begin{bmatrix} a^{-2} & 0 \\ 0 & b^{-2} \end{bmatrix}\begin{bmatrix}a\\ b\end{bmatrix}}{\begin{bmatrix} a^{-1} \\ b^{-1}\end{bmatrix}} = \begin{bmatrix} 1 \\ 1 \end{bmatrix}.
$$
I haven't seen this definition you've given using elementwise division of vectors, and I believe the canonical component-wise condition number would be a norm of this "vector condition number". (e.g. Using the $\infty$-norm, $\kappa_2(f(a,b);(a,b)) = 1$.) Using the component-wise condition number, the problem seems perfectly well-conditioned! What is going on here?
The standard vanilla norm-wise condition number measures approximately how much we expect the relative error between $f(x+\Delta x)$ and $f(x)$ to be compared to the relative error between $x$ and $x+\Delta x$. Specifically,
$$
\mbox{relative error in $f$} \le \kappa \cdot (\mbox{relative error in $x$}) + \mbox{higher order terms}.
$$
If we say $(a+\Delta a, b+\Delta b)$ has a relative error, say, $10^{-6}$ in the $\infty$-norm compared to the true value $(a,b)$ this means that the errors $\Delta a$ and $\Delta b$ in each component are less than $10^{-6}\|(a,b)\| = 10^{-6}a$. Note that if $a$ is more than $10^6b$, then this means the error $\Delta b$ can be larger than $b$ itself! But when we actually evaluate $f$, $a^{-1}$ is much much smaller than $b^{-1}$ but $b$ has been perturbed by a large error $\Delta b$ and thus the relative error in $f$ (largely dominated by the relative error of $b^{-1}$ is very high. In effect, if one considers norm-wise relative error, the relative error of small components of a vector can be made very large and these large component-wise errors can be amplified if $f$ depends on the small entries of its input.
In many practical settings, we have an input vector for which every component has small relative error. For example, if the errors $\Delta a$ and $\Delta b$ are the result of approximating arbitrary real numbers $a$ and $b$ by floating point numbers, we have that $|\Delta a| \le \epsilon |a|$ and $|\Delta b| \le \epsilon |b|$ for a small constant $\epsilon$. Thus, this worst-case scenario in the last case is impossible, but there's no way to prove that using norms as, if we only assume, $\|(\Delta a, \Delta b)\| \le \epsilon \|(a,b)\|$, there's no way to show $\Delta b$ is small relative to $b$. Component-wise condition numbers do exactly this. They allow you to measure the conditioning of a problem relative to small component-wise perturbations in the input, which allows one much better control over the relative error in small values in the input vector.
At the end of the day, I still have to say the line "we can employ the second condition number when the first one provides a 'pessimistic' result" because there's not a catch-all heuristic to definitively show when componentwise conditioning will or won't give a substantially better error bound. However, I hope that the example I've given is a revealing illustration for how norm-wise conditioning can give misleadingly pessimistic error bounds for a problem and how component-wise conditioning can give more realistic bounds.