Those all sound like a pain in the butt guys. fordmugg you got the most nerve racking. I have NO problem backing up, and a quarter mile isn't that far but DOWN a hill would be a little icky i think.
As for illegal sized trailers here is a good pic for ya. My dad did this when the truck was his.
We moved that shed (over 9.5ft wide and almost exactly 14.5ft high) home from a park about 3 miles away. We only had to move one powerline! LOL