If you send circular polarized light into a QWP the output is always linear, and the axis of the linearly polarized light is determined by the orientation of the waveplate and the handedness of the light. It does not depend on the overall phase of the input. In particular it will be polarized on one of the diagonals that split the two axes (fast & slow) of the waveplate, and which diagonal depends on what handedness light you put in.
To see this a bit more mathematically, think about how you describe circularly polarized light mathematically and what a QWP does. If I decompose my light along the two axes of the waveplate, then it is $\vec{E}=E_0(\sin(\omega t),\sin(\omega t \pm \pi/2),0)$, where the $\pm$ is one sign for each handedness. The QWP will add some uninteresting net phase to these to oscillating components and a difference of $\pi/2$ (if it's a zeroth order QWP, else $\pi/2+2n\pi$) to one of the axes (depending on which axis is fast). If you consider both handedness cases on the input, you get:
$$
\vec{E}_{LH}=E_0(\sin(\omega t),\sin(\omega t - \pi/2),0)\rightarrow QWP\rightarrow E_0(\sin(\omega t),\sin(\omega t-\pi/2+\pi/2),0)=E_0(\sin(\omega t),\sin(\omega t),0)
$$
$$
\vec{E}_{RH}=E_0(\sin(\omega t),\sin(\omega t + \pi/2),0)\rightarrow QWP\rightarrow E_0(\sin(\omega t),\sin(\omega t + \pi),0)=E_0(\sin(\omega t),-\sin(\omega t),0)
$$
And as you can see both inputs are linear but rotated 90 degrees from each other.
All of this is linear optics, so in general you can treat each polarization independently, figuring out how they would each individually be transformed through each waveplate, and then add them back up at the end. Also, note that the light before the QWP in your example is also elliptically polarized. For exact calculations, and in general for more complicated systems, using Jones matrices is a good approach, as suggested by Alfred Centauri in the comments, although I'm not sure such a heavy-handed approach is necessary, you can probably just do it by hand like I just did.
For a measurement, taking data points with the polarizer will tell you the relative magnitude of the ellipticity but not the handedness of it, but you should be able to figure out the handedness e.g. by measuring with and without the QWP you suggested at an appropriate angle and seeing the direction in which the ellipticity deflects.