I found on my recent 3500 mile tow that if I cranked and shifted P to N and turned off and recranked and shifted P to N and off again that it seemed to shift smoothly back to 2H. Don't know but it seemed easier???
We are over 2000 miles into a trip flat towing our Jeep. Crank, shift to neutral, turn off, shift from 2H to N, crank, check R and D, shift to Park, lock and go. Sometimes very difficult to shift back to 2H once disconnected, but getting easier each time.
I have Roadmaster baseplate with Roadmaster Night Hawk towbar and Invisibrake for my 2018 JLU Sport. We have a 40' diesel pusher. We towed about 500 miles over last weekend and it did perfectly. Unfortunately, the purchase of the pieces and then price to professionally install does add up, but...
I have my 2018 JLUSportS equipped with Roadmaster face plate, Roadmaster Night Hawk tow bar and Invisibrake . Towing behind a 40' diesel pusher. I have only towed about 60 miles so far, but will tow over 400 miles over this coming weekend.