Motivated by recent experiments, we study the dynamics of a qubit quadratically coupled to its detector, a damped harmonic oscillator. We use a complex-environment approach, explicitly describing the dynamics of the qubit and the oscillator by means of their full Floquet state master equations in phase-space. We investigate the backaction of the environment on the measured qubit and explore several measurement protocols, which include a long-term full read-out cycle as well as schemes based on short time transfer of information between qubit and oscillator. We also show that the pointer becomes measurable before all information in the qubit has been lost.