Lets just go back to basics here.
Your mass M is just a vertical force which is M x g, so lets call it F1.
At rest / static, the pressure in the whole system is the same, so the equation F2 x A2 = F1 x A1
Now to get this mass to move upwards, you need to apply more force at F2, lets call it Fm.
The amount of Fm is variable depending on the velocity Vm of the Mass. This movement of the fluid creates a pressure drop in your constriction.
I think it should be easy to create an equation whereby movement of the F2piston creates a volumetric change, assuming this is a fixed F2 velocity, which results in a pressure increase in the F2 chamber. There will be an increase in the F1 chamber, but it is much lower and only really the piston friction so you can probably ignore it or add 10%.
So then solve fr different velocities of F2.
I still don't really know what is your variable that you are trying to find?