I know this statement has been made before around here, but IMO no towing combination should exceed the GCWR for the tow vehicle. Doing so could expose you to liability in an accident.
I just sold a toy hauler, 39 feet, with an empty weight of 12,700 and a gross weight of 17,200. I used a Ford F350 with Tow Boss rated for 26,001. In most states 26,001 lbs is the magic number you can tow without a commercial license. People selling trucks will claim they can tow the White House, so take that into consideration. Has the horse owner ever weighed the trailer with all the horses in it? Maybe, maybe not.
This thread will offer a lot of opinions, pro and con. Mine are:
Short bed trucks can tow fifth wheel trailers using a sliding hitch. Use a dealer to install the equipment, they can be dangerous if mis-installed.
If you buy the truck first, look for trailers that fit the towing numbers and ignore the anecdotes RV dealers will tell you about what you can tow.
IMO don't carry everything including the kitchen sink because you now own a fifth wheel with lots more storage. I never towed with water in the tanks, and I could have had nearly 200 gallons of fresh and waste combined if I wished. The old adage about whatever you start has to eventually stop should never be forgotten.
Invest in a pinbox for the trailer that absorbs shock. Do a search for videos on "chucking" to see the effects of creating a hard connection between a truck and trailer pinbox. After being slammed around for a couple of hundred miles on our first trip to Florida, I bought a MorRyde pinbox, best money I spent on the trailer. I don't understand why the manufacturers don't put them on all fifth wheels.
My last comment is to take some time now and look at fifth wheels before you buy a truck. It's a lot easier to find a vehicle if you have a good idea about what sort of trailer you want in the future. The truck will easily tow the TM until you make the purchase later.
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