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Looking at specs for the truck and generator, a ram 2500 4X4 with 6.4 Hemi and 4.10 gears has the following rating
3610 lbs for regular cab long bed
3300 lbs for crew cab short box
3140 lbs for crew cab long box
2910 lbs for mega cab short box
so looks like the MEP-005a weighs about 2850 lbs...
to answer the question of "how dicey..."
if the pavement is dry the entire way you'd probably be okay if you have a lot of trailer towing experience, and added some extra weight in the bed of the truck to help keep the trailer from pushing you around.
If it's wet pavement and you have to make...