Three issues: Width, turning radius, tie downs. The trailer will be wider in this orientation and may be pron to be hit by a passing car on a narrower road. Due to the very short tounge one of the leading edges of the trailer will hit the back bumper when making a large turn. The ties downs will extend out making the trailer even weirder ( I don't see tie down facilitation on this trailer picture).
What about a regular trailer that stands up. Go to Kendons trailers web site.