Not having password-less ssh really a bummer. I'm considering chromebook as I've been doing remote dev on EC2 instances for many years already, and the workflow you described here is no alien to me. My current macbook air just a gateway to real development machine where I just need browser and iterm most of the time.
Searching around however I found this where it possible to use ssh key with Secure Shell, where the key has to be generated on other machine.
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