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That’s an interesting question. I haven’t gone on >200 mile road trips with this cargo carrier/haven’t had to Supercharge.

That being said, recall it can only carry a hundred pounds on the Tesla hitch so it’s very easy to simply take it off (like literally a moment) and set it aside if need be.

There are quite a few superchargers where you can drive in (like at the end of a row) or through (like in the middle of a parking lot) so there’s that, too.
I’ve gone on several long trips with the hitch rack mounted. It is indeed a challenge but I haven’t had the need to dismount anything so that I could SC. I always had my wife stand in the back to guide me as close to the chargers as possible.