I could make a case on both sides of this and depends on a couple factors. I would not recommend buying a new truck based off the information thus far.
Yes, a bigger truck will typically always be more advisable. Especially with a long and tall trailer. The HD truck will be a night/day towing difference.
Next, are you over weight? What is the reasoning for considering a bigger truck?
It's possible you could be towing within the limits of the truck (need more info to know for sure) and if so I would not think a truck upgrade is "needed". Again, a bigger truck could always be advisable...
If you are within the weight limits and you feel comfortable driving the half ton, then we are back to asking the reasoning for the question of a bigger truck.
It's very feasible that even towing within the weight limits of the truck, you still may not be very comfortable with the tow vehicle. In that case, a transport, rental, or brand new truck could all be a reasonable solution.
If you do not want to tow overweight regardless of how "okay" she drives, then the bigger truck is always advisable.
In the end, nobody can tell you if you "need" a bigger truck, or if you are "ok" with the half ton. Seems everyone has their own tolerance for towing. Your best case for a bigger truck is if hit the scales and find that you are overweight. Putting yourself and others at risk and being overweight is not a good combo.
For me, when I towed at capacity and didn't want to get pushed/pulled all over the interstate in a half ton truck, I tried taking a side route on state highways with lower speed limits and less traffic.
Good luck!
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2016 Road Warrior 355
2015 Ram 3500 Cummins SRW 4x4 MegaCab ShortBed
2011 F150 ecoboost - Traded
2015 Jayflight 28 BHBE (sold)
2009 Jayflight 26 BH (sold)
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