First note that
$$
\frac{1}{k^2}\le \frac{1}{k^2-1/4}=\frac{1}{k-1/2}-\frac{1}{k+1/2}.
$$
So over any range of $k$,
$$
\sum_{k=M}^{N}\frac{\log^2 k}{k^2}\le \log^2 N\sum_{k=M}^{N}\left(\frac{1}{k-1/2}-\frac{1}{k+1/2}\right)=\log^2 N \left(\frac{1}{M-1/2}-\frac{1}{N+1/2}\right),
$$
since the sum telescopes. In particular, for any increasing sequence of indices $1 \le M_0 < M_1 < M_2 < \cdots$, we have
$$
\sum_{k=M_0+1}^{\infty}\frac{\log^2 k}{k^2} = \left(\sum_{k=M_0+1}^{M_1} + \sum_{k=M_1+1}^{M_2}+\cdots\right)\frac{\log^2 k}{k^2}\le \sum_{i=1}^{\infty}\log^2 M_i\left(\frac{1}{M_{i-1}+1/2}-\frac{1}{M_i + 1/2}\right)\\=\frac{\log^2 M_1}{M_0+1/2}+\sum_{i=1}^{\infty}\frac{\log^2 M_{i+1}-\log^2 M_i}{M_i+1/2}.
$$
If we take $M_i=2^i$ for $i\ge 0$, we get the bound
$$
\sum_{k=2}^{\infty}\frac{\log^2 k}{k^2} \le (\log^2 2) \sum_{i=0}^{\infty}\frac{(i+1)^2-i^2}{2^i+1/2}=(\log^2 2)\sum_{i=0}^{\infty}\frac{2i+1}{2^i+1/2}\approx 2.475,
$$
which isn't bad. Most of the error is at the low end, so treating the first few terms exactly will improve things. In particular, take $M_i=2^{i+b}$ instead. Then
$$
\sum_{k=2}^{\infty}\frac{\log^2 k}{k^2} \le \sum_{k=2}^{2^{b}}\frac{\log^2 k}{k^2} + (\log^2 2) \left(\frac{(b+1)^2}{2^b+1/2} +\sum_{i=b+1}^{\infty}\frac{2i+1}{2^i+1/2}\right).
$$
For $b\ge 10$, this bounds the original sum below $2$. (As others have pointed out, hardly a middle-school problem... but at least this estimate uses a telescoping sum in some capacity.)