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@skierdude The length is probably an insurmountable issue. The comment about making the trailer higher off the ground to flow more air under it would make matters far worse. Not only would it raise the trailer's center of gravity making it less stable all by itself, it would increase air turbulence increasing lift and also serve to increase the sail area making the trailer more reactive to cross-wind. If anything you want to effectively reduce the height of the trailer. Just look at all the semi trailers with skirts along the sides. They can't lower the height of the trailer so they do the next best thing, they reduced the turbulence underneath. I've never seen a TT with skirts but you get the idea.

You've already gotten good advice in this thread regarding weight and balance as well as WDH and stabilizers.

Everything else you can try is going to be an expensive experiment. The stock tires on the trailer might not be the best quality, you can try upgrading them with an eye to the stiffest sidewalls you can find. Same for the Ascent. I'm not actually telling you to do this, because I doubt that it will be a cure. Just trying to give you an idea that fixing physics is going to be trial and error and there are costs and risks to be considered.
 
Take a look at the Winnebago Micro Minnie 1800BH. It's not a panacea, but has more tolerable specs: dual axle, queen bed, and bunks. It's still pushing it a hair on the length (21'11") but the 3660 dry weight and 382 hitch weight are a bit better.

Disclaimer: I have no experience with this trailer, I've just seen it discussed here before.

 
I started a post a few weeks ago with many of the same issues. I've got a 23ft Surveyor and was experiencing sway and steering issues above 60 mph. I've done several tests and another trip varying the total trailer weight and tongue weight. I believe that my set up is about at the limit for the Ascent. I've found that keeping the total weight about 4500 or 4600 lbs and the tongue weight in the low 400's and if I keep my speed at 55, I can drive safely with no sway (except when getting passed by some of the semi's on the interstate doing 70+) and no stress. Since we only plan to use the trailer for short excursions (under 300 miles) I'm ok with continuing to use the Ascent. If we were to take an extending trip, I'd opt for a truck to pull the TT. I had expected that Subaru was conservative in their weight limits, but I don't believe they are. The 5000/500 is tops.
 
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