If you really want the Scalade with you, you can buy a open drive up trailer for about 4,000 that will handle the weight of the caddy and is completely safe for the drive line as all four wheels are off the ground
Yea, I'm with Sloppy D here. Once you disconnect the drive lines and go some place, you're going to have to reconnect them when you get to your destination to drive the truck. Not sure about you guys, but when I leave the house on vacation, I like to vacation not work underneath the truck. Plus before you leave to go home, you'll have to disconnect them again for the return trip.
Living close to Chicago where its common to miss a no parking sign or misinterpret parking permit hours or something similar, I'm worried about getting towed in the city and then having to pay for a new transfer case. I parked my SLS in a bad spot one night and the damn tow driver smashed into the front of the car when he picked it up which drove the front of the car back against the tires. So when I got to the pound I had to pay $150 for the tow and I found out the car wasn't drivable which meant paying $125 for another tow out of the pound to a body shop and giving the shop $250 to stretch the front end back out. After discussing things with a lawyer, he said there are TONS of cases against the pound in small claims court, but most of the plaintiffs don't win becuase its City of Chicago vs. a City of Chicago judge and they normally help each other out. After threatening the pound, they gave me $100 back. Gotta love Chicago politics.
Anyway, if you want to roll with the Caddy, an open trailer is the way to go.
Oh, and would it be more fuel efficient to tow the coach with the 'lade?? Something to think about...