I have no idea if your claims are true, and I am not a specialist of the two systems above. Nevertheless, one can make the following observations.
For the first system ("shallow water"), the eigenvalues of the flux's Jacobian matrix are $\lambda_\pm = q \pm \sqrt{\rho + q^2}$. Therefore the system is strictly hyperbolic if $\rho + q^2 > 0$. The gradient
$
\nabla \lambda_\pm = \pm\left(\tfrac12, \lambda_\pm \right)^\top / \sqrt{\rho + q^2}
$
of the eigenvalue $\lambda_\pm$ is never orthogonal to the corresponding right eigenvector $(-\lambda_\mp/\rho, 1)^\top$ over the domain of hyperbolicity. Therefore, both characteristic fields are genuinely nonlinear, and the Riemann solution is a combination of shocks and rarefaction waves.
For the second system ("Chaplygin gas equation"), the eigenvalues are $(q\pm 1)/\rho$. Therefore, the system is strictly hyperbolic if $0 \neq |\rho| < +\infty$. The gradient
$
\nabla \lambda_\pm = \left(-\lambda_\pm, 1 \right)^\top /\rho
$
of the eigenvalue $\lambda_\pm$ is always orthogonal to the corresponding right eigenvector $\left(1/\lambda_\pm, 1 \right)^\top$ over the domain of hyperbolicity. Therefore, both characteristic fields are linearly degenerate. You may find the articles (1-2) interesting, which may present a similar problem.
(1) H. Cheng, "Delta Shock Waves for a Linearly Degenerate Hyperbolic System of Conservation Laws of Keyfitz-Kranzer Type", Adv. Math. Phys. (2013), 958120 doi:10.1155/2013/958120
(2) D.-X. Kong, C. Wei, "Formation and propagation of singularities in one-dimensional Chaplygin gas", Journal of Geometry and Physics 80 (2014), 58-70 doi:10.1016/j.geomphys.2014.02.009