I started years ago on a 1985 500cc Honda Shadow. I was lucky I didn't dump the bike in the guys driveway when I took it for a test drive as I hadn't been on two wheels, especially motorized wheels, since I was like 13 years old riding mini-bikes across fields.
I then skipped several years after getting hit by a car on this same bike while stationed in Japan, and finally bought an `03 Road Star Silverado (1600cc). Again, lucky I didn't dump it when leaving the dealer as I hadn't been on two wheels, especially wheels this size/weight, in about 10 years.
Loved my Star, especially the fact I could actually work on it myself if I wanted to. Never had a problem, and enjoyed pulling into a parking lot full of Harleys with a bike that didn't get lost in the crowd. Problem was, the suspension didn't suit my wife's bad back, so she was suffering.
We started looking at Ventures and sort of climbed the price range until we test drove an Ultra and ended up with the `08 Ultra we have now. I still had the Star at the time and after riding the Ultra a few weeks I climbed back on the Star and it felt unbalanced, weighty, and really bulky. Though even after having the Ultra for almost I year I'll still say my Star felt far more powerful than my Ultra does.....though I'll be making some changes to it soon so that this statement is no longer true.
The Ultra is definitely more comfortable, on short and long rides. I didn't buy it because it's a Harley, but for the comfort on long rides for my wife. But after having it now for not quite a year, HD WILL definitely be my first choice when I go to get a bike for me to ride solo.
Since my wife is a Brit, we have a US and a UK flag on the back, so even in a sea of Harleys it still stands out so we can find it easy!
Though, with the stock pipes on it, there's not a huge difference in how it sounds to me going down the road than my old Star did when it was stock. But I'm sittin' on it, not behind it. And just as I did with my Star, I'll be swapping the stock pipes for some real ones sooner or later.