IMO you are comparing apples to oranges. I owned an Ultra Classic about 5 years ago. I bought it as an investment from a friend and ultimately waited till he got on his feet and sold it back to him for what I paid.
I have also owned a Heritage Classic, Dyna wide glide and 1200 Sportster.
Now don't get me wrong here. Harleys are just bad arse to look at and to ride. There is no other bike in the world other than a custom built machine that can provide the enjoyment of a Harley.
But that is as far as a Harley will take you. I bought my 08' Goldwing for a purpose. I wanted a machine that had Power, Comfort and Dependability.
I would never attempt a trip more than a couple hundred miles on a Harley. And I learned that if you plan to ride it daily, you better not drive in traffic. They are HOT and they WILL overheat easily unless you spend a lot of $$ in tunes, pipes, ect. You can get them to run cooler but they will still overheat in Texas traffic. And unless you fork over some serious $$ for the 101ci engine, they just do not have the power to pull hills or 2 up with a trailer as easily as the Wing does.
All this being said, I love my wing!
BUT, I do plan to buy another Ultra Classic for weekends and local runs around the Casa! Like I said, you just can't beat the feeling of a loud rumbling Harley. They are a joy to ride and it just brings on a whole new persona when you ride it.
But for serious touring and 2up, it's the Wing that we will be riding. Smooth as butter, more power than you'll ever need, comfortable as all get out, great fuel mileage and piece of mind knowing you can ride a couple thousand miles with no fear of breaking down.
So I say, do what I am doing and own BOTH OF THEM!!