I've read that $$ \sum_{k=2}^{\infty} \frac{1}{k (\log k)^2} = 2.1097\ldots $$ However when I compute the partial sums it looks like a lot of terms are needed to even get the first decimals right.
My question is : how many terms do we need to sum in order to get, say, the first $5$ digits right ?
If you are satisfied with an approximate answer:
The function $t \mapsto \frac{1}{t(\log t)^2}$ is strictly decreasing on $(1,\infty)$, so for $n \geqslant 2$ we have
$$\int_{n+1}^\infty \frac{dt}{t(\log t)^2} < \sum_{k=n+1}^\infty \frac{1}{k(\log k)^2} < \int_n^\infty \frac{dt}{t(\log t)^2}.$$
Substituting $u = \log t$, we obtain
$$\int_x^\infty \frac{dt}{t(\log t)^2} = \int_{\log x}^\infty \frac{du}{u^2} = \frac{1}{\log x}.$$
To get within $\varepsilon$ of the sum of the series, one needs $\frac{1}{\log (n+1)} < \varepsilon$, or equivalently $n > e^{1/\varepsilon}-1$ at least, and $n > e^{1/\varepsilon}$ is certainly sufficient.
It is a little unclear what error we can accept to get the first five (significant) digits right, but the error must be $< 10^{-4}$, and an error of $5\cdot 10^{-5}$ will probably produce the first five correct digits. That means we need at least the terms to
$$k = \left\lfloor e^{10^4}\right\rfloor \approx 8.8\cdot 10^{4342},$$
and for the smaller error of $5\cdot 10^5$, we need the terms to
$$k = \left\lfloor e^{2\cdot 10^4}\right\rfloor \approx 7.756\cdot 10^{8685}.$$
There is no way to get the first five digits correct by summing the series naively within the lifetime of the universe using computers resembling the currently available ones.
To find the sum, one can approximate the series (after a reasonable number of initial terms) by the integral and estimate the error made by the approximation.