A few weeks have elapsed here and I have given a lot of thought to this thread. As a Honda Pilot owner and former Rockwood Roo 183 owner, now (coming this week!) 2306 owner this is probably the most valuable thread I have ever read.
Hondaman174,EXGMTech, bikendan, KDHfan, gave a lot of thought to your comments and reading between the lines here, I decided to trade in the Pilot for a new 2014 Durango with the HEMI. It wasn't easy to find a nicely appointed SUV with a 3rd row that fits in my city driveway, but I can honestly say that the Durango is a stellar TV. My tow rating with the Durango is 7400lbs or thereabout, ample room to pull the 2306 and I can load it up comfortably with all my gear, water, and no concerns.
Talk about an expensive ordeal! But I'm square on this now.
Bottom-line, the Honda Pilot can handle the Rockwood Roo 183 or 19 without problems, and while I can't vouch for pulling the 2306 with the Pilot, it could probably handle it, but why take that chance.