Welcome to the forum and congrats on your new Jeep. Regarding the leak on the passenger side, this is not uncommon but I recommend you take it back to the dealer to have it checked. Often it's a simple seal issue. Regarding the hitch and wiring hookup, I question the dealer. On my '04 I was able to get the harness I needed through Mopar and installed it myself by just following the direction sheet. I cannot believe an '08 was designed in such a way that it would have to be rewired. Check on the Quadratec or the 4WD Hardware websites for harnesses and hitches. See if anyone at either place can tell you the right answers. They usually know for certain. Hope that helps! Again, welcome!