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Hey, this is gonna sound really stupid to you all I am sure, but, can you stack two extenders on each other? like say I have a double wide, and I put a double tall on top of it, this wouldn't work would it?
Sure, you can stack them any which way you want, along with all the parasitic capacitance/inductance/resistance and cross-talk to go with it. It depends on what you stack. This doesn't create new pins so various devices won't necessarily work together just because you have the extenders, you'll have to recompile the code to available I/O lines which are dependent upon the hardware the code uses as well.
For very low speed devices (relative to system clock speed) you won't have issues generally, as the frequency of whatever signal is passed on a particular line goes the complexities increase really fast.