Did you lower the front end as well? If yes, which kit did you use? I used the Harley kit on my 09 UC front and back and I'm bottoming out two up with luggage. Are the progressives that much stiffer?I have an 09 Ultra Classic as well. I went with the Progressive 412 HD shocks in 12.5". I was amazed at the difference a half an inch made. Stock shocks are 13" eye to eye. I ride two up most of the time and I have had no problems of bottoming out.
I would really like to see those boots with the extra thick soles and heels!