I wish you provided these pictures and information earlier, there was not any need for long discussions.
I do not know the maximum operating pressure and temperature. The pipe will absolutely expand in axial direction under thermal load. The bonding between pipe and insulation, and between insulation and polyethylene cladding will be effective. If their bonding resistance is greater than polyethylene-soil bonding resistance the pipe with insulation and cladding will thermally expand in the soil. If it is the other way around pipe will move axially in the insulation. I trust your company have already experience on this and I cannot add more. The compaction will not be problem for this type insulation and cladding.
You mention there is field cold bending with the insulation and cladding. I would expect the insulation inside the cladding will rubble under the concentrated forces during bending if the local forces are more than the compressible allowable of the insulation, but will still remain there. Field bending may be problem for small radius turns. I suppose you need to see adequate lifting not to cause crashed insulation in the cladding for the same reason.
You still need to provide the insulation dry for all the insulation (factory or field), otherwise the corrosion will be problem.
I did not have experience this kind of application earlier, I trust, David's comment is valid. I do not have the software to try and see it unfortunately.
We learn every day.
Good luck.