I'm a bit confused on the question...
If the trailer is to go on rollback (failed axle, frame issue), the trailer needs to be in the 20's in length max to fit on the rollback (and they do make different bed lengths). The tongue would sit up close to the cab, and the axles need to be on the bed.
If you are needing to tow both the tow rig and the trailer, the TV would be on the bed (most will fit a crew cab long bed truck), and the wheel lift (if the truck has one) will be used to pull the trailer. Any wheel lift I've seen has a tow ball option for a trailer. As for the overhang from a truck bed, just extend the wheel lift for clearance between the downed TV and the front of the trailer.
