I have never seen a Tesla charging station that would allow a pull-through. With an 11,000 pound pulling capacity you could have something in the range of up to close to 30 feet long. It will be interesting to see how Tesla figures that out. Do we even have an idea of what the range is...
90%? What other trailer connectors are there that you would tow with a pickup truck? The 4 pin is for trailers without electric trailer brakes and the 7 pin is with.
Remember nothing is free. The whole charging thing is a mess and will not get better soon and I expect it will only get more expensive as time goes on.