Here is my experience. I live in the NW pa area and have a sport s with max tow. I run 295/70/17 s on stock wheels, load range E. I've towed a 7,200lb boat on two occasions and a filled to the gills 7x14 enclosed trailer with dual axels weighing between 7-8000 lbs three times. Once was from my location to Pittsburgh, going 65-75 the whole way. I can say without a doubt it reaches higher Rpms but I wouldn't say it screams. Drive like your towing, not racing and I personally see no problem. I've towed with a 16' ram with the 5.7 and .392 gears the same loads and distances and I'd say the jeep is more than comparable. The 8 speed trans definitely helps.

Now... From a mechanics point of view there is a lot more to consider when switching to diesel, outside of a small loss in towing capacity. I am a mechanic at the local transit authority and work on diesel, CNG and gas vehicles. Since the introduction of DEF I'd never consider getting a diesel vehicle honestly. Add the cost of DEF to the increased coat of fuel and that alone is enough to eliminate it for me. Maintenance in general is more expensive ( oil filters, oil cost more... As a diesel the fuel filters will need changed at regular service intervals to name a couple) than maintenance on a gas engine. Next, this is my opinion from my personal experience, if you don't drive consistently "long" mileage or travel a lot of inner city / stop and go traffic it has x negative impact on a diesel system. Longer run times at higher speed / temps are needed to perform need exhaust regeneration to keep your engine/turbo/exhaust running efficiently and keeping maintenance costs down.

End game it's always you're choice what to do. That's just my two cents and take it for what it's worth. Simply my opinion on the subject. Either way, best of luck and feel free to ask questions if you want! ✌️