That is still a bit scary for me.
1: you are already tail down, and you haven't added a load yet.
2 your proportions are all out of whack, the trailer is driving the tahoe (assuming a 4500 lb trailer)
A 10,000 lb trailer means two 5200 lb axles, not the weight of the trailer. Thats a max combined wieght rating. An open deck 10k GVWR trailer is usually about 3500 lbs unladen, enclosed is a little more. A 25 foot race trailer from haulmark for example is about 3700, 28 = 4200 and a 33 = 4700 lb...
assuming that is a 33 and your weight estimate of 2500 is correct (small 60s british roadster, small tubeframe car, honda) you are going to wind up with roughly an 8000 lb load, if there are no spares & no extra bodies, nothing but you and the car and trailer.
That is doable.
Most people grossly underestimate the actual 'WET' weight of a vehicle. A muscle car is closer to 4000 lbs, not 3200, for example. add fuel, tools, jacks, and passengers/crew and you can be looking at a 5000-5500 lb load + trailer = 9500-10000 lbs.
That's why you need a 10000 lb trailer to carry a single car to the races.
Trailers like that were honestly never meant to be hauled by close coupled ultra SWB SUVs. Those are meant for 3/4 ton LWB pickups, or 1 ton LWB pickups, even better if it is a crew cab longbed. IE trucks with full floating axles, and heavier duty transmissions, and a longer moment arm to better control sway and keep the trailer from driving the tow vehicle down grades, under braking, or in windy conditions. A suburban is about the same wheelbase as a LWB single cab, while a Tahoe is even shorter than a swb single cab pickup.
Doesn't mean you can't get away with it occasionally, but if this is going to be frequent (every weekend) or very long distance (over an hour or two), you'll want a real tow vehicle. 3/4 ton turbodiesel or a 1 ton turbodiesel slick.
Personally, I would weigh the trailer, both before and after you load it. You can easily figure out your your hitch weight (10%), and you'll want a weight distributing hitch and DEFINITELY an Anti sway device and an aggressive setting on the brake controller.
Sucker sure needs the ass aired up about 2 inches higher in the air. I also hope you have LT rated tires on the Denali.
Anyway, good luck whatever you decide to do.
