You have to be very careful when you ask for people's input on the internet. Facts have a way of quickly becoming blurred with opinions. This is especially true with towing where there are
very strong opinions and biases.
It all boils down to actual facts. With the VIN number, you first find the rated towing capacities of your specific truck. You'll get the maximum payload and tow rating. Never exceed either, in fact, try to stay 80% or more below them for an extra margin of safety. If you do this, you should be fine.
A 1500 is a considerably better tow vehicle than an SUV or car, a 2500 is a considerably better tow vehicle than a 1500, a 3500 is a considerably better tow vehicle than a 2500. And a semi rig is a considerably better tow vehicle than a 3500. All of this is inconsequential. The only thing that really matters is
properly matching the tow vehicle to the trailer.
So, let's take a look at your specific case. You're looking at a 2021 Warlock Classic Bighorn, crew cab, 5.7, and 3.92 gears. You said you don’t know the specific payload yet. Get the VIN off of the Maroney sticker and look it up. For the sake of this discussion, we'll go with the RAM published capacities, they may be less depending upon the options, but it should be fairly close. Be sure to use the VIN-specific specs when you do your final calculations though.
So, with a 1,439 lb maximum payload and a maximum towing weight of 10,230 lbs, let's see how that compares with your trailer.
You stated a Gross Vehicle Weight for the trailer at around 8300 lbs. That's 81% of the Warlock's maximum towing capacity, so you're good to go there. The next hurdle is the payload. You didn't state the loaded tongue weight of the trailer. That's critical and without it, we can't properly qualify the trailer. But let's run an estimate. If the GVW of the trailer is around 8300 lbs as you say, you're going to need at least 10% of that weight on the tongue for safety, so that's 830 lbs. Let's say 900 lbs, just to be safe. That would give you 530 lbs left for additional truck payload. If you could stay within these limitations, you would be safe to tow. If you can't, then it's a no-go.
This ends the factual section of this post. The rest is just my opinion, so please take it as such.
The last factor is the trailer's size. At 35 feet, you're definitely pushing it for a 1500. It would probably be best to stay 30 feet or below. With an excellent weight distribution hitch and anti-sway system such as a Hensley Hitch, you could possibly push it to 35 feet, but it's a stretch and it may be uncomfortable driving at times.
I think your weights might be ok but the length is a bit too long. Personally, I wouldn't recommend anything more than 33 feet max with a 1500 and that's with an exceptional anti-sway WDH.
In my opinion, your trailer is as big as anyone should go with a 1500, at least for a comfortable towing experience. I would either stick with your 2500, or get the Warlock and a slightly less large trailer.
