I see this thread is a few months old, but thought I'd reply anyhow. I've only had this bike a little over a week. 07 CVO Ultra Classic. And, I've noticed on a few occasions a front end wobble riding by myself.
I checked the air pressure in the shocks. They were at "0". I added 15 lbs of air, figuring that would be a good amount for a 205 lb guy. This last two days, no wobble so far. I'm commuting with the bike around 27 miles each way on mostly freeway, so I'll remain vigilent on how it is handling. It should not wobble at any speed. I too have the leather, thus heavier trunk.
Any other observations since May?