Here's my take on trailering.
Expect Gross Tow weight to exceed 5,000 pounds. While a
Class III hitch will handle up to 8,000 lbs, sufficient for a loaded CD 25 and trailer, many pickups are not rated high enough. For instance, my Honda Ridgeline is rated at 5,000 only. It's a similar size of a "half-ton" truck. I found a site that lists ratings for various trucks. A 2016 F-150 is rated at 5,000 pounds/500 pounds tongue weight. A 250 is 6,000, and increases to 8,000 only if powered by a 6.7 liter engine.
That site is here:
http://news.pickuptrucks.com/2015/11/kn ... imits.html
A couple sites say that with a weight distribution system on the trailer the ratings increase. By that theory, my Honda would be appropriate for 8,000 lbs, as it has a Class III hitch. The problem isn't, in my opinion, getting the tongue weight manageable, and isn't even the power, it is braking, power for hills, and gas mileage, or lack there of. Here in Georgia, dual-axle trailers are only required to have one axle with brakes. I had a nice Trident trailer with brakes on both axles. I towed a boat that brought the gross towing weight up around 5,000 lbs. It worked okay. but even with two braking axles, there was a dramatic increase in stopping distance. Additionally, gas milage dropped way off, as did speed going up hills. AND it was terrible in winds. Thinking about it, the boat I hauled was fairly low profile. A sailboat will be higher, therefore more affected by winds.
Another consideration is the net weight of the towing vehicle. My Honda is fairly heavy. A lighter weight truck, in theory, would reduce the gross combination weight, helping out on braking, speed up hills, and gas mileage. However, it also increases instability in winds, and emergency braking situations.
My brother, after buying a fifth-wheel trailer, found his gas-powered Chevy 250 deficient. It didn't have the power he wanted and gas mileage was horrible. He traded it for a 250 diesel. He's happy with that, and considers it the minimum for towing around 6,000 lbs.
Given all that, if I wanted to trailer Cassandra (CD25) with my Honda, I wouldn't hesitate to do so. Rating are, well, made to be exceeded. (I shall forever deny I said that.) It's a matter of knowing what to expect, being careful, and many years towing experience.
My two-cents worth. Yours may vary.
All the Best. Terry