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I like the idea of trusted devices, but being a security minded IT guy, I worry about the number of devices people *cough*FoxKat*cough* setup. Trust enough devices and suddenly your phone is unlocked almost everywhere and you're no more secure than you'd be if you just left it unlocked all the time.
That said, sometimes I get tired of putting in a PIN and I set my lockscreen back to swipe to unlock (which I did for YEARS before becoming so security minded).
There's definitely a trade-off between security and ease-of-use, so you've got to decide for yourself where to draw the line so that you're comfortably protected, but not completely inconvenienced.
Just take a little common sense to be as secure as you can be while still utilizing things like trusted devices. Do something like taking advantage of the feature outlined in the OP, and you definitely shouldn't keep your Chromebook and your phone in the same bag while out and about. Someone swipes your bag and suddenly they've got your entire life and it's unlocked for their thieving pleasure.
I don't think so...I think the corporate account policies take precedence and you are forced to always swype / pin / password, etc. I could be wrong though...I don't have a corporate account on my Maxx and my new work phone (soon to be) does not have Trusted Devices....but again...does this stuff even work if, for example, you have a corporate email account on your device that forces a PIN-lock on your phone?