$\gamma$ is the (triangle) contour $i\longrightarrow-i\longrightarrow1\longrightarrow i$. $\def\rmd{\mathop{}\!\mathrm{d}}$
Using Mathematica to evaluate the directional limit at $0$ on $\gamma$ Limit[1/Sin[1/z], z -> 0, Direction -> -I]
I get $0$. [Proof: $z=iy,\lim_{y\to0}\sinh\frac1y=\infty\Rightarrow\lim_{y\to\infty}\frac1{\sinh\frac1y}=0$]
So the integrand is bounded and continuous on $\gamma$, so the integral is finite.
Using Mathematica to evaluate the integral NIntegrate[1/Sin[1/z], {z, I, -I, 1, I}]
I get $$\int_\gamma\frac{1}{\sin \left(\frac{1}{z}\right)}=\frac{i\pi }{6}$$ I try to prove this.
Sum of residues at $z=\frac1{\pi n},n=1,2,\dots$ $$\sum _{n=1}^{\infty }\frac1{\frac d{dz}\sin(1/z)|_{z=1/\pi n}}=\sum _{n=1}^{\infty }\frac1{-\frac{\cos(1/z)}{z^2}|_{z=1/\pi n}}=\sum _{n=1}^{\infty } \frac{(-1)^{n+1}}{\pi ^2 n^2}=\frac{1}{12}$$ Then $$\int_\gamma\frac{1}{\sin \left(\frac{1}{z}\right)}\rmd z=2\pi i\cdot\frac{1}{12}=\frac{i\pi }{6}$$ Is this proof correct? I am worried since $f(z)$ has a non-isolated singularity at $z=0$.