Okay, so here's some feedback on towing a 34' 9979 lb GVWR TT with a Chrysler Aspen Limited Hemi.
They got a 1400 lb WD hitch, sway control and Activator II brake control, which we installed and set up in the driveway. Oh yeah, he picked up a pair of clip-on mirrors. Then they revealed the plan was to travel to a lot they'd purchased 1500 km away in New Brunswick! This is with 2 adults, 4 little kids, a dog and a bunch of stuff. Kids these days are fearless.
The only previous towing experience he had was utility trailers and a rented box trailer behind a minivan. From a few texts exchanged, it looks like they reached their destination with 1 overnight stop (they left at 8 p.m.) and had no problems along the way. Initially he had to tweak the brake controller en route and tighten down the sway control because we had loosened it to get out of the driveway. The Aspen also has its own electronic trailer sway control.
So, I appreciate all the warnings, but it appears this marginal combination did the job. Their plan is to set up the trailer there semi-permanently and return without it within a couple of weeks.