In this work we use the formalism of chord functions (i.e. characteristic functions) to analytically solve quadratic non-autonomous Hamiltonians coupled to a reservoir composed by an infinity set of oscillators, with Gaussian initial state. We analytically obtain a solution for the characteristic function under dissipation, and therefore for the determinant of the covariance matrix and the von Neumann entropy, where the latter is the physical quantity of interest. We study in details two examples that are known to show dynamical squeezing and instability effects: the inverted harmonic oscillator and an oscillator with time dependent frequency. We show that it will appear in both cases a clear competition between instability and dissipation. If the dissipation is small when compared to the instability, the squeezing generation is dominant and one can see an increasing in the von Neumann entropy. When the dissipation is large enough, the dynamical squeezing generation in one of the quadratures is retained, thence the growth in the von Neumann entropy is contained.