It only takes 2 people to push a Legends car into a trailer, so no need to drive it in.
In my opinion, single axle is pushing it with an enclosed trailer, since they will have 3750# or less axles.
Benefit of a single axle (in Wisconsin at least) is that it doesn't have to be registered.
I was a little worried about being able to pull my 16x7 enclosed with my tired 4.8L Tahoe, but it doesn't have a problem