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I for one can tell you that you can have all the truck in the world and the weather can put you in the ditch.

While pulling my sled trailer in a bitoch of a snow storm, the road iced over. We were doing about 25mph and the cross winds would push my 29ft enclosed off the road. Truck kept getting pushed sideways. Made it to the next town with a hotel and got a room for the night. $100 room for the night was cheaper than the deductible on the the truck and trailer.

We stopped counting all the cars/ and trucks in the ditch after a while.

That might have been the first and only time I wish I would have had an open trailer.
 

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Id rather have AWD than 4x4 pulling on snowy or icy roads. Especially windy roads that are patchy ice.

Ive felt the rear end get loose pulling my trailer. Ive felt the rear end slip without a trailer. Both times on clear roads with one rogue ice patch. So I was in 2wd. So yeah if I could get a pickup with awd I probably would.

Shorter wheelbase with full time awd is better than rwd with a longer wheelbase in that situation imo. Thats the situation that will put someone in the ditch. The longer wheelbase and traction control does a good job of keeping it straight. But if it had awd, I bet that situation wouldnt even happen most the time.

Your well within the towing capacity. Sounds like your well experienced in towing. I think he will be just fine lol theres always the guys who feel the need to beat their chest about how their pickup truck makes them better at towing. A guy towing a 2 place enclosed with a well setup and level trailer in a Q5 full time awd is safer than a guy with a pickup, who slaps the trailer onto a hitch that points the nose up in the sky and has no clue where to put the weight inside the trailer barrelinf down the road at 80mph.
 

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2014 ZR8000lxr 21-22 mileage 500mi
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Pickup with AWD - Honda Ridgeline towing capacity 5000lbs. AWD with Super Handling built in. Good tires instead of the stock Firestones will take you anywhere till it's packed to the frame. (BTDT with a 64' Landrover 109)
 
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