Hi Cahdbiker! I'm with you, loving the low end grunt of the SE 255's, so I was reluctant to swap them out with the SE 585's, knowing they might lose that off the line torque. Ron at RC Cycles suggested that we try a 4 degree advance on the cam, and boy was he on the money.
My bike is just as fast off the line, I can still easily pass cars in 6th gear (I'm a 3k rpm at 80mph, so I'm right in the power band), and yet it extends the power at higher rpms. I've lost nothing (but heat), and maintained torque further across the board, while picking up a modest 9hp. I'm very happy with the results, as I was already happy with the 110 performance (Not happy with some of the crappy components (cam bearings, lifters, flywheel tolerance, etc.) Moco puts in these bikes.
If I would have had any serious engine failure, (my bike is off warranty), I would probably go straight to a S&S T124LC granite.
Here's the dyno overlay of my SE255's with my new SE585's!

In my 09 I am sticking with my 255s and Fulsac stage one kit. I would hate to lose that bottom end and I usually shift by 5k anyways. I would ask anyone who installed 585s in a SE Ultra Classic to chime in and give an opinion. Or call S&S and ask them. CAHDBIKER