Main Question
We can telescope the first sum:
$$
\begin{align}
\lim_{N\to\infty}\sum_{n=1}^N\left[\psi\left(\frac{n+1}2\right)-\psi\left(\frac{n}2\right)-\frac1n\right]
&=\lim_{N\to\infty}\left[\psi\left(\frac{N+1}2\right)-\psi\left(\frac12\right)-H_N\right]
\end{align}
$$
In this answer it is shown that $H_{-1/2}=-2\log(2)$; therefore, $\psi\left(\frac12\right)=-2\log(2)-\gamma$.
Asymptotically, $H_n=\gamma+\log(n)+O\left(\frac1n\right)$; therefore, $\psi(x)=\log(x)+O\left(\frac1x\right)$.
Thus,
$$
\begin{align}
&\lim_{N\to\infty}\left[\psi\left(\frac{N+1}2\right)-\psi\left(\frac12\right)-H_N\right]\\
&=\lim_{N\to\infty}\left[\log\left(\frac{N}2\right)+2\log(2)+\gamma-\log(N)-\gamma+O\left(\frac1n\right)\right]\\[4pt]
&=\log(2)
\end{align}
$$
A Formula For Later Use
Starting with
$$
\begin{align}
\psi(x)
&=-\gamma+\sum_{k=0}^\infty\left(\frac1{k+1}-\frac1{k+x}\right)\tag{1}\\
&=-\gamma+H_{x-1}\tag{2}
\end{align}
$$
we get
$$
\begin{align}
\psi\left(\frac{n+1}2\right)-\psi\left(\frac{n}2\right)
&=\sum_{k=0}^\infty\left(\frac1{k+\frac{n}2}-\frac1{k+\frac{n+1}2}\right)\\
&=2\sum_{k=0}^\infty\left(\frac1{2k+n}-\frac1{2k+n+1}\right)\\
&=2\sum_{k=0}^\infty\frac1{(2k+n)(2k+n+1)}\tag{3}
\end{align}
$$
Using $n=1$ and $\psi(1)=-\gamma$ in $(3)$, we get
$$
-\gamma-\psi\left(\frac12\right)=2\log(2)\tag{4}
$$
which is an alternate proof that $\psi\left(\frac12\right)=-2\log(2)-\gamma$.
Supplementary Question
We can apply $(3)$ to
$$
\begin{align}
&\sum_{n=1}^{2N}(-1)^n\left[\psi\left(\frac{n+1}2\right)-\psi\left(\frac{n}2\right)-\frac1n\right]\\
&=-\log(2)-\gamma+2\sum_{n=1}^N\left[\psi\left(n+\frac12\right)-\psi(n)\right]-\psi\left(N+\frac12\right)\\
&=-\log(2)-\gamma+4\sum_{n=1}^N\sum_{k=0}^\infty\frac1{(2k+2n)(2k+2n+1)}-\psi\left(N+\frac12\right)\\
&=-\log(2)-\gamma+4\sum_{n=1}^N\sum_{k=n}^\infty\frac1{2k(2k+1)}-\psi\left(N+\frac12\right)\\
&=-\log(2)-\gamma+4\sum_{k=1}^\infty\sum_{n=1}^{\min(k,N)}\frac1{2k(2k+1)}-\psi\left(N+\frac12\right)\\
&=-\log(2)-\gamma+4\left[\sum_{k=1}^N\frac1{2(2k+1)}+\sum_{k=N+1}^\infty\frac{N}{2k(2k+1)}\right]-\psi\left(N+\frac12\right)\\
&=-\log(2)-\gamma+4\left[\frac12\left(H_{2N+1}-\frac12H_N-1\right)+\frac14+O\left(\frac1N\right)\right]-\psi\left(N+\frac12\right)\\
&=-\log(2)-\gamma+\left[2H_{2N+1}-H_N-1\vphantom{\frac1N}\right]-\log(N)+O\left(\frac1N\right)\\
&=-\log(2)-\gamma+\left[2(\gamma+\log(2)+\log(N))-(\gamma+\log(N))-1\vphantom{\frac1N}\right]-\log(N)+O\left(\frac1N\right)\\
&=\log(2)-1+O\left(\frac1N\right)
\end{align}
$$
Thus, changing the sign and taking the limit, we get
$$
\sum_{n=1}^\infty(-1)^{n+1}\left[\psi\left(\frac{n+1}2\right)-\psi\left(\frac{n}2\right)-\frac1n\right]
=1-\log(2)
$$