My understanding regarding stiffness is that a very stiff fin reacts like a higher percent carbon mast reacts to flex very quickly, thus i think they can get on the plane earlier. It does not handle chop very well and makes the board uncomfortable, also can be prone to spin out.
Regarding the likes of deboichet it's like buying a porsche or a WRX both very good performance cars one just costs a lot more. I believe the deboichet's can make coffee also

Regarding a quiver of cheap fins - you will get the greater range and some improved handling by having the different sizes - but the good custom fins should give a greater performance when compared to the cheapies performance. How much? Unsure, but it does exist - I've noticed changes from the stock fins to customs on my slalom gear. ultimately it is a price thing and a personal sailing preference, just because the local fast guy uses one type of fin does not necessarily mean that it will work for the type of sailor you are.
Experiment, experiment and experiment.