OK I drive truck and I pull double trailers , and I have no problem keeping my tail trailer behind me it is very stable. I have also had the misfortune of having my heavy trailer as the tail a few times and guess what nothing happen. It just went down the road fine.
Now some one on here posted about the setups they us in Michigan and how they have a fifth wheel on the back of the trailer, I think that's what is called a B train and there a nice set up for flat beds but not so nice for van trailers.
Now the set up I pull use two 28 foot long trailes. The two trailers are hooked together with what's called a converter dolly. Its called converter dolly because it converts a semi trailer to a full trailer. Now a semi trailer is a trailer were some of the weight is carried by the tow vehicle. A full trailer carries its full weight on its axles and little to no weight is carried buy the tow vehicle.
OK the lead trailer is hooked to the truck with a fifth wheel hitch. The converter dolly is hooked to the lead trailer with a pintle hitch than converter dolly is backed under the tail trailer with the truck and lead trailer. And the dolly is hook to the tail trailer with a fifth wheel hitch.
As far as backing everything up well it can be done it just takes time and practice.
Sorry for the long post I hope this helps clear up a few things