Great write up. In 2003 I did exactly what you did, tried out several Harleys with the same results. I looked like a monkey humping a football on the Sportster. The only ones that really tripped my trigger were the Fat Boy and the Road King, but I didn't have the 18-25K it would have cost.
I went to another dealer and found a new T100. It was love at first sight and 7.5K.
We had 10 great, trouble free years together. Almost all of my friends ride Harleys and they liked my bike, even though they treated me like the demented uncle who lives in the attic.
I just moved on to a 2012 Thunderbird Storm. I love it, but I will never forget that Bonneville