Yup, you could definitely have this problem!
I have a 2015 Silverado 2500HD, SRW, short bed with a Demco Hyjacker Autoslide hitch. The hitch has three height settings and I have to have it in the highest position. Otherwise, the rear of the Trail Air Tri Glide would hit the side rails if I turned beyond about 45 degrees. The setup results in the front of my trailer being about 3 inches above level (towing nose up), but it has not negatively affected the way it tows.
There are various models of the Trail Air, and maybe the Flex Air doesn't have this problem, but my Tri Glide (Model L07) does. (It seems to be a design error to me.) I wasn't able to find it online. Maybe it is no longer available.
Except for having to tow nose high, I do like the ride the Flex Air provides.
2015 Crossroads Rushmore Springfield
2015 Chevy Silverado 2500HD Duramax