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I own a 2011 Pilot 4WD that I’ve been using for work as a carpenter. It’s worked well with the large cargo space until now, and I’m finding I want a trailer as I further expand my business. I’m looking at a 5 x 10 enclosed trailer with a 990 dry weight/ 2990 gross weight. The manual states I should be able to tow 4300 pounds with a passenger, but I figure 4000 is a safer number since I’ll have some cargo, my helper is fat (jk) etc. So on paper this works, but my question is, how much is this going to potentially suck as a daily tow? Is the vehicle more meant to occasionally tow a boat or RV, or will it stand up to towing daily? Will an enclosed trailer have too much wind drag to make it a reasonable drive on a consistent basis? If you have real world experience, advice would be appreciated. If this isn’t practical, I may need to upgrade to a truck, though I love the Pilot.
 

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It's rated to do it. If you have been on top of maintenance and fluid refreshes it should work just fine. Will it last as long as a 1500 or HD pickup towing the same trailer? No. Will it feel more stressed and strained making low speed maneuvers up steep driveways or staying at speed on the highway? Yes.

Again, it can do it but it just won't be as happy about doing it and likely won't last as long as something with more capability.

Assuming business is good, that's why you are looking at a trailer - I'd look to start saving money towards a new or used work truck and hopefully the Pilot lasts long enough that you have plenty saved up.
 

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Never been a huge fan towing with my Hondas. I believe towing to be just an afterthought. It's just not that great towing with a vehicle that has the engine sideways under the hood.
If I needed it for my work, I'd use my Pilot with my eyes out for something more suitable. I'd keep the weight in the trailer as light as possible without overloading the tounge. Change the ATF often using Full Synthetic Valvoline MaxLife.
 
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