299 ft is the max. for cat5 cable which is heavily shielded. I wouldn't try cat3 over that length.
A second jack will not fix your problem! The problem is with the wiring in the first jack. The wires are mixed up so the xbox and your router don't get the "link up" signal which is required for negotiating frame size, transfer speed etc.
I don't know about this leviton RJ45 but from pictures it looks like a color coded snap-in jack. I guess your friend just connected the matching colors which should result in the "link down" problem you experience. That is if I'm right about the jack.
Unplug the RJ45 jack from your router and look at the second pin from the left. You should see a wire through the clear plastic which is either green or orange (don't mix up with brown which is pin

.
If the wire on pin 2 is green connect the RJ45 jack like this:
Wire - Leviton RJ45
-----------------------------------
green orange
green-white orange-white
orange-white green-white
orange green
If the wire on pin 2 is orange on the router side just switch the table above.
Just for the records I was wrong about the used wires. Worked to much with other cable for the last few monthes

The wires utilized are 1,2,3 and 6.
EDIT:
Is it
this what you've in your living room?