Interesting thread... All the more so considering I just left the bank after selling my Dodge 2500, and booking a flight to go pick up my new (to me) Lexus 450.
I have a Starcraft 14RT offroad pop-up toyhauler, and a 31' Airstream. The Starcraft is about 3000 loaded, and the Airstream about 6000 loaded dry. I plan to tow both with the 450, but only the Starcraft for longer trips. I will use a WD hitch for both. The Airstream will only be towed on the flats for 100 miles or less with the Lexus. I think even that will be a bit of a test.
Like the OP, I am careful, and also licensed to drive any combo of semi-trailers that are on the road. That and $1.79 will get me a coffee at Starbucks... If I can get the 31' trailer parked!:sombrero: