I recently got a new workstation at work that is a MacBook Pro that connects to 2 monitors via USB-C.

I've learned somewhat superstitiously that if I don't connect and disconnect the USB-C cables in the right order the laptop may stop responding and I have to do a hard reboot. I thought this solved the problem but even now it still occasionally happens.

Your question makes me wonder if something like this isn't the cause (Mac misreading USB-C signal).

If all devices actually follow the standard, then yes, a device should be able to detect a cable was plugged in even if the other end is disconnected. The trouble is finding compliant hardware, I fully expect it will be at least 2 more years before we start seeing common hardware that follows the spec.

The plug can have (has?) resistors that let the socket "feel" it, even if the cable is not attached to anything.

Yes, the cables are active and can ID themselves when connected. Detection of another connected device (and orientation) is separate.

So yes, it is possible to detect which end gets connected first, but this absolutely shouldn't have any side-effects. It is unintuitive and fragile (if the 'master' device restarts, it will think the other end connected first, suddenly becoming 'slave').

Just imagine this: Device A <--> Device B

Device A receives the cable first, upon receiving the cable, Device A notices that the cable is not "hot" ("hot" in the sense that there is voltage/activity on the wire), so then Device A decides to "turn on" the cable, make it "hot".

Now Device B receives the cable, it notices that the cable is already "hot" and decides that it must be the second device.

I would imagine it could work that way,

Im also pretty sure that the usb cables are "dumb" cables and not active cables like QSFP (these have chips at each end).