I have never ridden a Harley on the freeway with strong crosswinds, but..... It is really impossible to make direct comparisons, because you can't recreate wind gusts that are the same in different comparisons. Whatever you think is happening is just perception.
The Harley tourers vs the Wing have about the same sized amount of side surfaces, and weigh about the same, so they should be about equal in that regard. The Wing might be a little more. If anything, the Wing's lower center of gravity should make up for any difference in size of surfaces.
From the front, the Wing has a distinct disadvantage in steady headwinds due to the size of the fairing and windshield. But in gusts, the Wing will be more stable due to its fixed fairing. Regardless of claims otherwise, the whole reason for manufacturers switching to frame mounted fairings is because it is a well known fact that fork mounted fairings are vastly inferior, and highly susceptible to steering instability when riding through gusty winds.
The bottom line is that, if cutting through strong winds from either the front or the side is a major concern, then neither bike would be a good choice.
Last edited by Sparky57; 06-18-2017 at 07:27 AM.