Firmware updates blow away any customizations. So you need to bootstrap things again after each update.
Updates can be deferred, so the process isn’t too disruptive.
Edit: oh, yeah I see what you’re getting at. That direction could work, and I used to do that years ago, as it turns out, but these days I am frequently not on a familiar WiFi network when I’m using the tablet, so cabling has been more practical.
IME IP addresses handed out by my phone’s tethering mode aren’t stable, so it’s sorta more of a hassle than just fishing out the little cable and letting my script run. (The device assigns itself a stable IP address on the USB interface.)
Although I haven’t looked at those addresses in some time; perhaps they are more stable now than they used to be.
It’s easier than that with the remarkable tablet — the device documents its current ipv4 and ipv6 addresses. But it’s several taps away, and then typing on the laptop keyboard, whereas USB is just a connector away. Plus, you need to charge anyways.
Updates can be deferred, so the process isn’t too disruptive.
Edit: oh, yeah I see what you’re getting at. That direction could work, and I used to do that years ago, as it turns out, but these days I am frequently not on a familiar WiFi network when I’m using the tablet, so cabling has been more practical.