That's my plan. I have a base SS on order but SL'd it through options. I think it will be a good match. Two of mine are carbon fiber and one is EGlass (standard material)...both aircraft grade composites. If I had it to do all over again, I would want all three out of EGlass as it finishes out better though carbon fiber sounds cooler. I've got roughly 100k miles between the three. These are the most aerodynamic full size m/c cargo trailers on the market. Roughly 27 cu. ft capacity, nice interior, on-board air compressor, on-board battery, uses Bosch relays and circuit breakers and weighs right at 200 lbs.. It has a patented pitch inertia drawbar which will be nice for the SS as the hitch will most likely be un-sprung (like the Spyder hitch...attached to the swingarm). They are so easy to pull, I never disconnect from it. The fellow that builds the Tailwinds has a demo trailer with about 250k miles on it and zero maintenance though he recommends checking them at 50k intervals...I'm going to service mine at 100k. I get 50-60k miles out of a set of tires.
E-Glass version...
I also have a CanAm trailer. I does have a good trailing arm suspension and is fairly aerodynamic. I had a Spyder too. It wasn't a keeper but the trailer was. I like the CanAm trailer due to it's depth. The two lids didn't work out so well in the rain (water on back lid gets dumped into the cargo area when it's opened) but it sounds like a bigger deal than what it is. This trailer is 22 cu. ft. of capacity.
I also tow camper trailers that would work fine behind the SS. These are Roll-A-Home campers...one is a single bed and the other is a king-size bed. These take about 2 minutes to set up, start to finish.
I highly modified the single. Has fridge/freezer, A/C, heater, lithium iron batteries, 8 gallon saddle tanks to transfer fuel on the fly, a pitch inertia drawbar morphed on it...a mobile command post.
Adequate storage under the tent section...

I made the bed..."you might be a ******* if your bed looks like lawn furniture". And that's my hotrod, turbo'd air conditioner.
With the OEM fuel tank, pillion auxiliary tank and trailer saddle tanks, I'm hauling 24+ gallons of fuel.
At this point, I'm obligated to work out a hitch for the SS. Anything I can tow behind a Wing, the SS will handle with ease and no stability issues.
Z