We derive a representation of the sum in question $f$ as a double integral with a symmetric integrand. Transformation to polar coordinates leads to a explicitly "innocent" expression for the integrand in the domain of interest.
It is proposed to develop the integrand into a power series. The developments are under way.
Letting
$$d(n)=\frac{1}{2 n}+\log (n)+\gamma$$
the nth summand becomes
$$s(n)=H(n)^2-d(n)^2$$
and the sum is
$$f=\sum _{n=1}^{\infty } s(n)$$
We now use the integral representations
$$d(n)\to \int_0^1 \left(x^{n-1} \left(\frac{1}{1-x}+\frac{1}{\log (x)}-\frac{1}{2}\right)+\frac{1-x^n}{1-x}\right) \, dx$$
and
$$H(n)\to \int_0^1 \frac{1-x^n}{1-x} \, dx$$
and replace the terms in the summand which then becomes a double integral (sorry for the bad Latex)
$$si(n)=\int _0^1\int _0^1\left(\frac{\left(1-x^n\right) \left(1-y^n\right)}{(1-x) (1-y)}-\left(x^{n-1} \left(\frac{1}{1-x}+\frac{1}{\log (x)}-\frac{1}{2}\right)+\frac{1-x^n}{1-x}\right) \left(y^{n-1} \left(\frac{1}{1-y}+\frac{1}{\log (y)}-\frac{1}{2}\right)+\frac{1-y^n}{1-y}\right)\right)dydx$$
The sum of $si(n)$ over $n$ can be easily done.
$$si=\sum _{n=1}^{\infty } si(n)$$
The result, called $sa1$ and is the integrand for the positive quantity $-f$ in what follows, is
$$\text{sa1}=\frac{\left(\frac{1}{1-x}+\frac{1}{\log (x)}-\frac{1}{2}\right) \left(\frac{1}{1-y}+\frac{1}{\log (y)}-\frac{1}{2}\right)+\frac{\frac{1}{1-x}+\frac{1}{\log (x)}-\frac{1}{2}}{1-x}+\frac{\frac{1}{1-y}+\frac{1}{\log (y)}-\frac{1}{2}}{1-y}}{1-x y}$$
Now we make two subsequent coordinate transformations
- x-> Exp[-u], y->Exp[-v]
- u->r Cos[a], v-> r Sin[a], 0<=r, 0<=a<=pi/2
This defines sa3. Instead of giving the lengthy expression we show the plot

The plot shows that sa3 is a pretty innocent function.
$-f$ is now given by the integral of $sa3$ over $r$ from $0$ to $\infty$ and over $a$ from $0$ to $\pi/2$.
A numerical check gives sufficient agreement between direct sum with 10^4 terms (|sum| = 0.392733) and this integral (int =0.392733 ) to see that the integrand is correct.
Expansion of the integrand in a series of powers of $(a-\pi/4)$
I was not able to do the integral in symbolic form (neither of the two). The plot shows, however, that the dependence of the integrand on $a$ is weak so that it seems reasonable to expand the integrand in a series of (even) powers of $(a-\pi/4)$ the coefficients of which are integrals over $r$ which seem not impossible to be done in closed form.
The first term of this development (equal to $sa3$ for $a = \pi/4$) is
$$sa3(a=\pi/4)= \frac{\left(\sqrt{2} e^{\frac{r}{\sqrt{2}}} r+\sqrt{2} r-4 e^{\frac{r}{\sqrt{2}}}+4\right) \left(5 \sqrt{2} e^{\frac{r}{\sqrt{2}}} r+\sqrt{2} r-4 e^{\frac{r}{\sqrt{2}}}+4\right)}{8 \left(e^{\frac{r}{\sqrt{2}}}-1\right)^2 \left(e^{\sqrt{2} r}-1\right) r}$$
Mathematica refused to solve that integral.
Behaviour of the integrand close to the origin
The behaviour of the integrand close to the origin is not easily found in the x-y-representation, but it is easy in polar coordinates: $sa3$ close to the origin is found by expanding it into a series of powers of $r$ and doing the a-integral exactly. The first four terms are
$$ \frac{\tanh ^{-1}\left(\frac{1}{\sqrt{2}}\right)}{3 \sqrt{2}} -r \frac{\pi }{48} -r^2 \left(\frac{1}{144}-\frac{\tanh ^{-1}\left(\frac{1}{\sqrt{2}}\right)}{240 \sqrt{2}}\right)+\frac{r^3}{480}+r^4 \left(\frac{149}{181440}-\frac{\tanh ^{-1}\left(\frac{1}{\sqrt{2}}\right)}{12096 \sqrt{2}}\right)$$
Numerically,
$$0.207742 -0.0654498 r-0.00434767 r^2+0.00208333 r^3+0.000769685 r^4$$
To be continued.