I simply take a felt-tip pen, and mark the side that goes up on each and every USB plug. Simple and cost-effective problem solving...
Not as simple, oddly enough I have come across PCs where the connections are flipped and also some PCs have the USB slots sideways and can also be flipped.
My news case has the most unusual ones yet. Even when I put them in right the slot on the cover seems to be just slightly gibber that the USB port so every time I still the USB connection it it gets stuck and since my PC is almost on the floor, it's completely black and I am usually in the dark in my room, it takes a few tries before it goes it, the USB plug that is (clear those dirty minds people, LOL).
I think this idea is cool but I can't help find some downsides to it. First I have to agree that the constant in and out of the side of the pins that's not connecting could eventually get messed up. I worry about that on my retractable USB sticks which have a similar concept.
Also how would this render smaller USBs which will now require extra space to accommodate the spring action and retractable piece? Not to mention how this would be useless for USBs that don't have the metal housing around it, that it's just the plastic piece with the connectors on it. Unless they are reversible and I'm not aware of that.