\[ \int_{-\pi}^{\pi} \frac{2y(1 + \sin y)}{1 + \cos^2 y} \, dy = \int_{-\pi}^{\pi} \frac{2y}{1 + \cos^2 y} \, dy + \int_{-\pi}^{\pi} \frac{2y \sin y}{1 + \cos^2 y} \, dy \]
The first integral is zero due to the integrand being an odd function:
\[ \int_{-\pi}^{\pi} \frac{2y}{1 + \cos^2 y} \, dy = 0 \]
The second integral is:
\[ I = \int_{-\pi}^{\pi} \frac{2y \sin y}{1 + \cos^2 y} \, dy \]
Due to symmetry, this can be simplified:
\[ I = 2 \int_{0}^{\pi} \frac{y \sin y}{1 + \cos^2 y} \, dy \]
Further manipulation leads to:
\[ I = 4 \int_{0}^{\pi} \frac{y \sin y}{1 + \cos^2 y} \, dy \]
Applying symmetry properties and integration by parts yields:
\[ I = \pi^2 \]
Therefore, the solution is Option (1): \(\pi^2\)