I would focus on how to get set up in Hawaii and forget about the Truck and trailer. Hawaii is way cooler place than any RV Park.
If Hawaii falls thru buy a used 5th wheel and the most truck you can afford.
All 2011 and newer trucks are great towing machines. The thing you need to watch though is how much weight they can carry. Can they carry the pin weight of the trailer plus tools, grill, cooler, people, dogs, canopy, kayaks, bikes, etc. etc.
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