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the specification for cat5 is 100 meters. HOWEVER, if you had to extend past that, if you have good quality cat5e cables, it is possible to run it farther. I wouldn't recommend it, because it -can- cause problems if you go too far, plus it takes forever to run a 500ft cable and to have it not work when its done would be a pain in the you know what. i have personally seen cat5e ethernet cables work over a gigabit network at 580ft without any drop in quality. now that that is said, heh..
if you are racking this stuff in a central location (building computer/server room) and both the 8-port and 16-port switch are going to be in this room, then no it will not add another 300ft to the limit. if you have the 8 port in the computer room and run a 300 foot cable out to the 16 port switch 300 ft away then you will have an extra 300ft on the other side of the 16port.
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