Recently in these pages we have had occasion to see the trigonometric identity $$ 2\arcsin\sqrt x = \frac \pi 2 + \arcsin(2x-1). $$ From this we can immediately deduce that $$ \sqrt x = \sin\left( \frac \pi 4 + \frac 1 2 \arcsin(2x-1) \right) $$ This suggests that the arcsine function near the left endpoint of its graph is shaped very similarly to the square root function. Part of this is obvious: it has a vertical tangent and is concave downward.
Sorry ‒ there was a typo in the question. What I intended is what the FIRST paragraph of the question was about; the second paragraph failed to be consistent with that since I left out the π/2 term. I've fixed it now.
But it makes me wonder about $x\mapsto \left(\frac \pi 2 + \arcsin x\right)^2$ near $x=-1.$ Is there anything interesting to say about an expansion of that function in powers of $(x+1)\text{ ?}$
Apply an integral representation and a binomial expansion:
$$\begin{align}\arcsin(x)&=-\frac\pi2+\int_{-1}^x\frac1{\sqrt{1-t^2}}~\mathrm dt\\&=-\frac\pi2+\int_{-1}^x\frac1{\sqrt{(1-t)(1+t)}}~\mathrm dt\\&=-\frac\pi2+\int_{-1}^x\frac1{\sqrt{(1+t)}}\sum_{n=0}^\infty\binom{-1/2}n2^{-\frac12-n}(-1)^n(1+t)^n~\mathrm dt\\&=-\frac\pi2+\sum_{n=0}^\infty\binom{-1/2}n2^{-\frac12-n}(-1)^n\int_{-1}^x(1+t)^{n-\frac12}~\mathrm dt\\&=-\frac\pi2+\sum_{n=0}^\infty\binom{-1/2}n2^{\frac12-n}(-1)^n\frac{(1+x)^{n+\frac12}}{2n+1}\\&=-\frac\pi2+\sqrt{2(x+1)}+\frac{(x+1)^{3/2}}{6\sqrt2}+\mathcal O((x+1)^{5/2})\end{align}$$
One can multiply a few of these terms out to get
$$\small(\arcsin(x))^2=\frac{\pi^2}4-\pi\sqrt{2(x+1)}+2(x+1)-\frac\pi{6\sqrt2}(x+1)^{3/2}+\frac13(x+1)^2+\mathcal O((x+1)^{5/2})$$
Of course, for the newly edited question, simply use the above expansion to see that
$$\left(\frac\pi2+\arcsin(x)\right)^2=2(x+1)+\frac13(x+1)^2+\mathcal O((x+1)^3)$$
And of course, the entire Cauchy product:
$$\left(\frac\pi2+\arcsin(x)\right)^2=2\sum_{n=0}^\infty\sum_{k=0}^n\binom{-1/2}k^2\frac{(-2)^{-n}(1+x)^{n+1}}{(2k+1)(2n-2k+1)}$$