I would like to try something like this, but I don't bobtail enough to matter. The "closing the gap part would need alot of work. because of when the trailer is at 90 degrees in relation to the truck when in a hard turn. Maybe there could be a work up of snaps up and down each side of the rear of the truck, and on the front of the trailer, then stretch an elastic/spandex material between the two so it flexes with flex and moderate turning. It still doesn't deal with hard turning.
A simple test boattail could be a large conduit rod starting at one side of the bottom of the cab, following the curvature of the sleeper up and over and back down the other side. Make serveral just like it, except taper them in each one. on the truck frame, make some type of flag pole holder to set them in while bobtailing. Just a driver's simpleminded perspective.
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