It might work if you didn't deviate from a straight line much. Imagine backing the trailer up until its at a 90 degree angle from the bike. Before you get to 90, the forks of the trailer will be horizontal and the trailer will be laid down flat.
I'd love to see a video of that setup in action. :wink:
If you look at the pivot angle on bob trailers you'll find most of them pointed slightly forward at the top. This results in the trailer tilting in the same direction as the tow vehicle during a turn. If your center of gravity is below the axis of rotation of the bob trailer, it will cause the trailer weight to want to twist the tow vehicle to a vertical position.