Tried it several years ago with a '93 EG Classic Anniversary... The tour pack extended beyond the loading ramp door jamb... It may work with removing the tour pack???

 

I second the suggestion to install a receiver hitch. You can buy one for less than $200 and put it on yourself in 15 minutes. I pulled a Massey fergusen 1429 tractor on a 24' trailer through some very steep mountains with my '06 F150 with a receiver hitch.

 

Plain and simple; a touring HD with the tour pack in the stock location will not fit into an enclosed 5x8 trailer with a square nose.

 

FYI if what you are refering to is the tow-ball being mounted on the bumper, U-haul will not allow this.

You need to have a properly rated receiver hitch, one where the ball and draw-bar slide into the hitch.

Doesn't matter what your bumper is rated for it's the way they roll...

 

I have a 5x8 and i had to cut and weld a trough in the front of the tralier as the ramp was hitting the very back of the tour pak...