Tesla should do what they can to provide at least one Supercharging stall at each location where charging can be done with the trailer hooked up. I have never had to unhook a trailer just to fill up at a gas station.
Maybe a small utility trailer or similar can be unhooked in "a minute." Chock the wheels, lower the jack, unhook the chains, unplug the lights, lift it off the ball. Hooking it up is going to take longer. Back up cameras help a lot. If the trailer is light enough that you can move it by hand, that helps.
But if it's a heavier trailer like a travel trailer with weight distribution, you aren't going to want to be hooking and unhooking it at Superchargers.
Towing our low-profile fifth wheel reduces our range by about 50%.