You need to use USB charger sockets that run from 12 V. They convert the 12 V to 5 V at the socket. As a result, the voltage drop isn't too important and they will give out 5 V even if the input voltage is a bit less than 12 V.
I don't know what the maximum current rating of the sockets will be, but they will consume about half the current that they give out.
(It's not magic, the power they give out is less than the power consumed. E.g. if the socket is giving out 2 A at 5 V, that is 10 W. If it is taking in 1 A at 12 V, that is 12 W, so it is losing 2 W in heat and it is 83% efficient)
There are various online voltage drop calculators that you can use. If you are connecting the -ve of the socket to ground near the socket, the length of the ground wire will be less. A lot of the calculators expect the ground and power wires to be the same length, so they show the combined voltage drop for both wires. For ease of calculation, assume that all the current is taken by the socket furthest from the supply.
rjenkinsgb advice is good. Having them in groups will keep the wire size needed down, and reduce the problems if there is a fault.
Also, those sockets all use some power keeping the 5 V converter working when there is nothing plugged in. You don't want them all taking current when the engine is off. Also, if one of the 5 V converters goes wrong, it could overheat, so you want to reduce the risk of that in an unattended vehicle.
It doesn't really matter whether you fit 1 or 100 sockets. 1 socket could flatten the battery if the vehicle is left for a week or two, and if the engine is running the vehicle's alternator will have no trouble keeping up with all the loads that 14 passengers are likely to bring along. So the answer to the question in your first post is that you can install as many as you like, as long as they are disconnected when the engine stops.