Inspired by the recent problem How to evaluate the sum $\sum_{n=1}^{\infty}\frac{1}{(2n+1)(2n+2)}\left(1+\frac{1}{2}+...+\frac{1}{n}\right)$ I asked for a generalization, and I found it with Mathematica.
Can you prove (or disprove) this heuristic finding?
Let
$$s(p,q) =\sum _{k=1}^{\infty } \frac{H_k}{(k+p) (k+q)}\tag{1} $$
Then
$$s(p,q)=\frac{1}{2p-2q}\left(H_{p-1}^2-H_{q-1}^2-\psi ^{(1)}(p)+\psi ^{(1)}(q)\right)\tag{2}$$
for $p\neq q$ and
$$s(p,q)=H_{p-1} \psi ^{(1)}(p)-\frac{1}{2}\psi ^{(2)}(p)\tag{3}$$ for $q =p $
Assuming $q>p>2$, from $\sum_{n\geq 1}H_n x^n = \frac{-\log(1-x)}{1-x}$ we have
$$\begin{eqnarray*} s(p,q)=\sum_{n\geq 1}\frac{H_n}{(n+p)(n+q)} &=& \frac{1}{q-p}\int_{0}^{1}(x^{p-1}-x^{q-1})\frac{-\log(1-x)}{1-x}\,dx\\&\stackrel{\text{IBP}}{=}&\frac{1}{2(q-p)}\left[(q-1)A_{q-2}-(p-1)A_{p-2}\right] \end{eqnarray*}$$ where $$\begin{eqnarray*} A_m = \int_{0}^{1}x^m\log^2(1-x)\,dx&=&\left.\frac{d^2}{d\beta^2}\int_{0}^{1}x^m(1-x)^{\beta}\,dx\right|_{\beta=0}\\&=&\left.\frac{d^2}{d\beta^2}\left(\frac{\Gamma(m+1)\Gamma(\beta+1)}{\Gamma(m+\beta+2)}\right)\right|_{\beta=0}\\&=&\frac{\pi^2+6H_{m+1}^2-6\psi'(m+2)}{6(m+1)} \end{eqnarray*}$$ leads to $(p-1)A_{p-2}=\zeta(2)+H_{p-1}^2-\psi'(p)$ and to OP's $(2)$.
Then $\lim_{p\to q}\frac{\psi'(q)-\psi'(q)}{q-p}=\psi''(q)$ and $H_{p-1}=\psi(p)+\gamma$ easily prove $(3)$, too.