It seems like hooking/unhooking is mostly about the backing up to match with the trailer, and the backup camera should help immensely with this. Maybe Tesla even has done some work to help in guiding the backing, but I wouldn't hold my breath.
The rest of the process should be easy and routine. The only time it would NOT be is if the trailer is huge and/or the tongue weight is too high.
There is a lot we don't know about towing with the MX, but one thing I can guarantee -- it will not be like towing with a giant truck where tongue weight is not much of a concern. You will have to have your load balanced very carefully to assure sufficient, but not excessive tongue weight. However, this is something that will not have to be re-done at every supercharger stop. Once you have the load set at the beginning of the trip, you won't mess with it.