Hmm, a mystery that needs solving. The trailer is a 550 Ultra with the SUV package. It is 2011 or older (door hinges give that away), but new enough to have a water access door on the side so likely 2005 or newer.
Looking at my customer list for WI for customers with 550 Ultra models those vintages and eliminating a couple I know are not this one I show 11 possibilities. Dang it, too many to narrow it down this time. I have my suspicions, I know of one customer with a dark colored Outback that might be it?
Cary