It's certainly the most raw and personal, to its benefit, but it's too unpolished to be as great as the others.
I wish he had remade it like a decade ago, after honing his style and technical talents, and with a right-sized budget. I'd still go see it if he did a remake now, but I doubt it would maintain enough of its spark at this point :)
Right, one of the many great things about Rushmore is that it is a mix of these. It's amazingly polished for someone's second movie. Like, that aspect of it shocks me every time I watch it. But it also still has a lot of that raw soul that Bottle Rocket does.