Definitely get the WDH, can't hurt anything and can only help - just check the manual, as mine specifically says I can't use any hitch devices (weird land rover thing).
Adaptive cruise probably has a couple issues - one of which is the fact that it (normally) brakes the vehicle if required. Using an electronic brake controller, I'm not sure if it'll activate the trailer brakes. Actually yours almost certainly has an integrated brake control system, but I'm still iffy on it allowing adaptive-cruise to modulate trailer brakes.
Trans shifting and hunting is probably also a big problem. On mine I can use command shift to lock in a certain gear and still use cruise control, but on a 10hr trip I only used it for a couple minutes. Like the last poster said, I feel way more comfortable being in control. Plus it's always good to have your foot near the pedals. Also almost any change in incline or speed required a gear change and totally different throttle, so I really couldn't let cruise do much of anything in command shift mode anyways. In auto w/ cruise it would almost certainly downshift one extra gear more than it needed to EVERY time there;s a speed change, which gets old really fast.
Also you might want to check the break-in periods and requirements in your manual since it's so new. Even though that's not a super large trailer, it'll definitely be the first work your SUV has ever had to do. :)