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I don't think the length will be a big deal. Going from an ultralight pop up to a 27' trailer WILL be a different towing experience. The push and pull of vehicles, the wind and sway will be something you have to get used to. I pulled my 37' trailer with my previous 1/2 ton and it did "OK" so I think the 27' will be fine. I use an Equalizer WDH/sway hitch and really like it.
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