I also installed a cool devise, the Thule Outrigger II
Curious how you manage not damaging the rudder with this device. Please advise your experience with the outrigger.
Just load the boat backwards to avoid potential rudder damage. The boat travels just as easily facing backwards as forward. You can use a small carpet or blanket to keep the bow from scraping on the deck. If the boat must face forward, mount the Outrigger on the rear bar and reverse the process.
Using a small step ladder open door or wheel well (standing on the tire), the boat can be flipped upside down once on top. Deck mounted items shouldn't be an issue as long as they don't stick out far, depending on your rack to roof clearance. Be sure to strap through the drivewell to insure that your boat can't slide off.