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I think the problem these connectors have is that each ring has to slide over the other contacts to get to its correct location.

USB Type-A has longer contacts for pins 1 and 4, the power pins, so they contact first and remain contacted before the data pins make contact. You can see that in this picture https://www.electroschematics.com/usb-how-things-work/.

Many of the TRS connectors have a built-in switch to (originally) disconnect the internal speaker.

It would probably have been easy to extend that concept to isolate all contacts until the tip hits the bottom.

That's not going to save you when you try to plug in the device-side connector with the computer-side already connected (and therefore already applying power to the cable).

Why? It's also disconnected at the device's socket until fully seated?

The iPod shuffle did this to decrease the connector size and count.

YES. TRRS would have been great. Or mini-TOSLINK

> I always thought a round ringed TRS style plug like headphones use would have been great. No way to orient it incorrectly.

Now consider the forward-looking bandwidth implications with that class of physical interconnect.