My basic idea is, that it might be possible to understand the series $S_k$ as composition of zeta-series where the arguments are negative integers and then assume, that that insertion of the negative integer arguments can be justified by some analytical continuation/zeta-regularization.
For instance beginning for k=2 with
$$ S_2 = 1\cdot 2 + 2 \cdot 3 + 3 \cdot 4 + ... \tag 1$$
then introducing
$$ \begin{align} {}
f_2(s) &= {1\cdot 2 \over 1^s} + {2 \cdot 3 \over 2^s} + {3 \cdot 4 \over 3^s} + ... \\
&= 2! \sum _{i=0}^\infty \binom{i+2}{2} { 1\over (1+i)^s}\\
\end{align} \tag 2$$
It is obvious, that there are continuous intervals for s like $ C_k \lt s \lt \infty $ with some fixed constand $C_k$ depending on k where this are convergent expressions. Then I assume, that it is meaningful to set
$$ S_2 = \lim_{s \to 0} f_2(s) \tag 3$$
as a limit-expression or by zeta-regularization or analytical continuation (don't know what the correct expression would be). I think that the general key for the analytical continuation is the said observation, that there is a continuous interval for s where the expression $f_2(s)$ is convergent - because for that s it can freely be decomposed into partial series.
Thus the goal is finding a composition of zeta's at s,s-1,s-2,... valid for continuously and infinitely many $s \gt C_2$ where the series is convergent and then let s=0 .
For the given example and some s (for $s \gt 3 $ this is convergent) we can then rewrite
$$ \begin{array} {rll}
f_2(s) &= \large {1\cdot 2 \over 1^s} + {2 \cdot 3 \over 2^s} + {3 \cdot 4 \over 3^s} + ... \\
&= \large { 2 \over 1^{s-1}} + { 3 \over 2^{s-1}} + { 4 \over 3^{s-1}} + ... \\
&= \large { 1 \over 1^{s-1}} + { 1 \over 2^{s-1}} + { 1 \over 3^{s-1}} + ...
& + \large { 1 \over 1^{s-1}} + { 2 \over 2^{s-1}} + { 3 \over 3^{s-1}} + ... \\
&= \zeta(s-1)
& + \large { 1 \over 1^{s-2}} + { 1 \over 2^{s-2}} + { 1 \over 3^{s-2}} + ... \\
&= \zeta(s-1) & + \zeta(s-2) \\
\to S_2 & \underset{\mathcal Z}{=} f_2(0) = \zeta(-1)+\zeta(-2) &= - {1\over12}
\end{array} \tag 4\\
$$
where $\mathcal Z$ means the zeta-regularization/ analytical continuation/ limiting-process.
For small k the sums $S_k$ can so be determined by -some tedious- manual pattern-detection, but the pattern-detection provides then also some simple general scheme where the zeta's are to be composed by Stirling numbers first kind which seems to be provable by relative simple compositions of matrices of binomial-coefficients and Stirling numbers.
Let $s_{r,c}$ denote the unsigned Stirling number first kind from the (infinite) array whose indices begin at zero
$$\Large S1 = \small \begin{bmatrix}
1 & . & . & . & . & . \\
0 & 1 & . & . & . & . \\
0 & 1 & 1 & . & . & . \\
0 & 2 & 3 & 1 & . & . \\
0 & 6 & 11 & 6 & 1 & . \\
0 & 24 & 50 & 35 & 10 & 1 \\
\vdots & \vdots & \vdots & \vdots & \vdots & \vdots &\ddots
\end{bmatrix} \tag 5$$
then the sums in question are expressible in closed forms as $$S_k = \sum_{i=0}^k s_{k,i} \zeta(-i) \tag 6$$
Similarly the $f_k(s)$ - versions are
$$f_k(s) = \sum_{i=0}^k s_{k,i} \zeta(s-i) \tag {6.1} $$
The results for the $S_k$ are then
$$\small \begin{array} {r|r}
k & S_k \\ \hline
0 & -1/2 \\
1 & -1/12 \\
2 & -1/12 \\
3 & -19/120 \\
4 & -9/20 \\
5 & -863/504 \\
6 & -1375/168 \\
7 & -33953/720 \\
\vdots & \vdots
\end{array} \tag 7$$
For a
further justification of this method I looked with the same scheme at the
alternating series $A_k$ istead of the original series $S_k$. Also using the alternating zeta-series $\eta()$ instead gives $$A_k = \sum_{i=0}^k s_{k,i} \eta(-i) \tag 8$$ and identical results pop up as when I do the sum of the explicite alternating series using Euler-summation. Here the results are
$$ \small \begin{array} {r|r}
k & A_k \\ \hline
0 & 1/2 \\
1 & 1/4 \\
2 & 1/4 \\
3 & 3/8 \\
4 & 3/4 \\
5 & 15/8 \\
6 & 45/8 \\
7 & 315/16 \\
\vdots & \vdots
\end{array} \tag 9$$
Final remark: it might be interesting, that the numerators and denominators of the $S_k$ are in the OEIS, see
numerators and
denominators (the numerators are given with alternating signs) and there is a whole bunch of furtherly interesting links and references!