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You can root a Chromebook if you choose to accept the risks involved. This is officially supported.

Sure, it's a nice feature, but I probably wouldn't. Maybe I'd put a sticker on it saying "my other computer is a Raspberry Pi Pico."

It's not necessary to root every device you own. You can use one to do your banking and web browsing and have entirely separate devices for hacking.

Unless you want to look like a criminal, I probably wouldn't carry around two phones everywhere you go.