Re: Tau Day: Because sometimes you just want to eat 2 Pi(es).
There's a video of him giving a guest lecture where he points out quite a few simple things.
One is a thought experiment where you notice a value 'h' showing up in all sorts of equations: area of a circle, kinetic energy, etc. it turns out that h = 1/2, so why make such a big deal over h, when 2h = 1 is a much more meaningful number.
I do think the selling point is as easy as noting that pi being half a cycle is not very logical. Plus, you can have a shape with constant "diameter" that isn't a circle, so it doesn't make as much sense for a circle constant factor as radius, which defines a circle.
Truth be told, I don't know what usefulness a diameter has, other than being waaaaaaay easier to measure in real life.