I just found this report and enjoyed it very much. Thanks for taking the time to lay it all out for us and for giving us those wonderful pictures.
If you haven't yet tried the Seat Concepts upgrade, you really should before you put in a lot more miles. I have their kit on my Super Sherpa and it is wonderful. I've since taken the bike on a couple of 500 mile trips and believe it or not, never even had to stand up. It is a real butt saver. It has a 'gripper' top fabric option which is great. No more sliding forward at every stop, cramming the boys into the tank. You park your butt and it stays parked.
Youth is wasted on the young.
The current herd:
2012 Honda NT700V for LD camping
1990 Honda VTR250 for scraping bar ends in the twists
2002 Kawasaki KL250 Super Sherpa for everything else