mr_andyj wrote:
IF you find a tow driver to tow a truck with trailer attached then u lucked out. Most will not even try, or most will say "insurance something so I can't".
A 5th wheeler is a different legal animal. In most States you can tow a 5th and attach a trailer to the 5th wheeler trailer, but if talking 5th wheelers then usually talking very big trailers to begin with.
Usually you will need trailer towed behind the flatbed or by another vehicle entirely. Don't count on the driver pulling your rig with a little tow truck.
The ability of the tow truck is not nearly important as what the driver is willing to do. Yes, a diesel can pull your rig easy, but no, the driver will probably not do both truck n trailer.
If you have a 5TH wheel, any heavy-duty wrecker and most medium-duties can tow the truck and trailer as a unit. I have seen it done many times. I personally rode in a wrecker that was towing a semi tractor hooked to a loaded 48' trailer, for about 65 miles. (Lost the water pump at 2am.)